Tricyclic compounds and method of treating herpes virus

ABSTRACT

The present invention provides a compound of the formula (I) and pharmaceutically acceptable salts having useful antiviral activity against viruses of the herpes family. In said formula, X=O, (CH 2 ) m , S, SO, SO 2 , NH, NR 8  or a chemical bond; Y=O, (CH 2 ) m , S, SO, SO 2 , NH, NR 8 ; Z=NH, O, NR 8 , S, SO, SO 2 . The remaining substituents are described in the specification.

FIELD OF THE INVENTION

[0001] The present invention relates to compounds possessing antiviralactivity against viruses of the herpes family, or a compositioncontaining them. These compounds provide a method for treating herpesviral infections, including condition caused by herpes simplex I such ascold sores, herpes simplex II such as genital herpes, as well asshingles caused by herpes zoster and infections caused bycytomegalovirus, Epstein Barr Virus.

BACKGROUND OF THE INVENTION

[0002] Various subfamilies of herpes viruses (Herpes viridae) exist:α-herpesvirinae, β-herpesvirinae, γ-herpesvirinae and cercopithecingHerpes virus I (B virus); some specific viruses are: Herpes simplexvirus-1 (HSV-1), Herpes simplex virus-2 (HSV-2), Cytomegalovirus (CMV),Varicella Zoster virus (VZV), Epstein-Barr virus (EBV), human herpesvirus-6 (HHV-6), human herpes virus-7 (HHV-7), human herpes virus-8(HHV) as well as others which may not yet be defined.

[0003] The incidence of infections by Herpes simplex virus is very highthroughout the world. Serological studies showed that herpes viralinfections affect a substantial percentage of the population.Reactivation of herpes virus infections may lead to recurrentinfections. The risk of severe diseases increases with decreasingimmunocompetence of the host. There is a pressing need for improvedtherapy for treating this disease. Currently, exclusive of vaccines,treatment involves primarily nucleoside drugs such as acyclovir, whichtarget thymidine kinase and suffer from development of resistance.

SUMMARY OF THE INVENTION

[0004] The present invention provides a compound of the formula and itspharmaceutically acceptable salts, or the compound and itspharmaceutical composition having useful antiviral activity againstviruses of the herpes family.

[0005] wherein:

[0006] X=O, (CH₂)_(m), S, SO, S₂, NH, NR₈ or a chemical bond;

[0007] Y=O, (CH₂)_(m), S, SO, S₂, NH, NR₈;

[0008] Z=N, NH, O, NHR₈, NR₈, S, SO, S₂;

[0009] n=an integer of from 0 to 2;

[0010] m=an integer of 1,2, or 3;

[0011] R₁, R₂, R₃, R₄, R₅ independently are hydrogen, halogen, hydroxyl,amino, mono or dialkylamino, cyano, nitro, alkyl groups (1-6 carbonatoms), alkoxy groups (1-6 carbon atoms), CF₃, OCF₃, aminoalkyl (1-6carbon atoms), aminoaryl, Oaryl, or a heterocyclic ring having 5-7 atomswith 1-4 hetero atoms of N, O or S;

[0012] Ar=phenyl,

[0013] substituted phenyl,

[0014] benzoheterocyclic ring,

[0015] substituted benzoheterocyclic ring,

[0016] heterocyclic ring, or

[0017] substituted heterocyclic ring, which have substitutions R₆ or R₇;

[0018] R₆ and R₇ are independently hydrogen, alkyl group (1-6 carbonatoms), cycloalkyl (3-12 carbon atoms), halogen, alkoxy, CF₃, aminoalkyl(1-6 carbon atoms), aminoaryl, or a heterocyclic ring of from 5-7 atomswith 1-4 heteroatoms of N, O or S;

[0019] R₆ and R₇ may also form a ring, optionally cycloalkyl or aryl orsubstituted aryl;

[0020] R₈ is hydrogen, alkyl (1-6 carbon atoms), cycloalkyl (3-12 carbonatoms), phenyl or substituted phenyl wherein the substituents are asdefined above.

[0021] The invention also provides for a pharmaceutical composition forthe treatment of infection or disease caused by a virus, optionally aHerpes virus which comprises an amount of the compound of claim 1sufficient to provide an antivirally effective dosage of the compound ofFormula I and a pharmaceutically effective carrier.

[0022] The invention also provides for a method of treatment ofinfection or disease caused by a virus, optionally a Herpes virus whichcomprises administering to a subject in need of such treatment aneffective antivirally dosage of a composition of formula I.

DESCRIPTION OF PREFERRED EMBODIMENTS

[0023] The present invention pertains to anti viral compounds. Preferredcompounds are as follows:

[0024] One preferred compound is:

[0025] Another preferred compound is:

[0026] Another preferred compound is:

[0027] Another preferred compound is:

[0028] Another preferred compound is:

[0029] Another preferred compound is:

[0030] Another preferred compound is:

[0031] The term “alkyl” means a straight or branched hydrocarbon radicalhaving from 1 to 12 carbon atoms unless otherwise specified andincludes, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl,sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl,n-nonyl, n-decyl, undecyl, and dodecyl. The alkyl group may beunsubstituted or independently substituted by from 1 to 3 substituentsselected from F, Cl, Br, I, OH, NH₂, SH, CN, NO₂, OCH₃, OCH₂CH₂OH,NHCH₃, or N(CH₃)₂.

[0032] The term “cycloalkyl” means a hydrocarbon ring, which containsfrom 3 to 12 carbon atoms unless otherwise specified, for example,cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl. Wherepossible, the cycloalkyl group may contain double bonds. The cycloalkylring may be unsubstituted or substituted by from 1 to 3 substituentsselected from alkyl, cycloalkyl, alkoxy, thioalkoxy all as definedherein, hydroxy, thiol, nitro, halogen, amino, formyl, carboxyl,nitrile, —NH—CO—R, —CO—NHR—, —CO₂R, —COR, aryl, or heteroaryl whereinalkyl (R), aryl, and heteroaryl are defined as herein.

[0033] The term “alkoxy” having 1-6 carbon atoms means a C₁-C₆ alkyl-O—group or radical wherein C₁-C₆ alkyl has the meaning as defined above.Illustrative examples of a straight or branched alkoxy group or radicalhaving from 1 to 6 carbon atoms, also known as a C₁-C₆ alkoxy, includemethoxy, ethoxy, 1-propoxy, 2-propoxy, 1-butoxy, 2-butoxy,2-methyl-1-propoxy, and 1,1-dimethylethoxy, 1-pentoxy, 2-pentoxy,3-pentoxy, 2,2-dimethylpropoxy, 1-hexoxy, 2-hexoxy, 3-hexoxy, and4-methyl-1-pentoxy.

[0034] The term “thioalkoxy” having 1-6 carbon atoms means a C₁-C₆alkyl-S— group or radical wherein C₁-C₆ alkyl has the meaning as definedabove. Illustrative examples of a straight or branched thioalkoxy groupor radical having from 1 to 6 carbon atoms, also known as a C₁-C₆thioalkoxy, include methylthio, ethylthio, 1-propylthio, 2-propylthio,1-butylthio and 1-pentylthio, 2-pentylthio, 3-pentylthio,2,2-dimethylpropylthio, 1-hexylthio, 2-hexylthio, 3-hexylthio, and4-methyl-1-pentylthio.

[0035] The term “aryl” means an aromatic carbocyclic ring having from 6to 10 carbon atoms. Illustrative examples of an aryl group or radicalinclude phenyl, 1-naphthyl, and 2-napthyl. The aryl group may beunsubstituted or independently substituted by from 1 to 3 substituentsselected, unless otherwise specified, from F, Cl, Br, I, OH, NH₂, SH,CN, NO₂, OCH₃, OCH₂CH₂OH, NHCH₃, or N(CH₃)₂.

[0036] The term “Oaryl” means an aryl-O— group or radical wherein arylhas the meaning as defined above. Illustrative examples of an Oarylgroup or radical include phenoxy, 1-naphthyloxy, and 2-napthyloxy. Oarylgroups may be unsubstituted or independently substituted by from 1 to 3substituents selected, unless otherwise specified, from F, Cl, Br, I,OH, NH₂, SH, CN, NO₂, OCH₃, OCH₂CH₂OH, NHCH₃, or N(CH₃)₂.

[0037] The term “halogen” means bromine, chlorine, fluorine or iodine.

[0038] The term “monoalkylamino” means an NH-alkyl group or radicalwherein alkyl has the meaning as defined above.

[0039] The term “dialkylamino” means an N-(alkyl)₂ group or radicalwherein alkyl has the meaning as defined above.

[0040] The term “aminoalkyl” having 1-6 carbon atoms means an H₂N-(C₁-C₆alkyl)-group or radical wherein C₁-C₆ alkyl has the meaning as definedabove. The aminoalkyl group is a substituted C₁-C₆ alkyl group orradical containing at least one substituent which is NH₂.

[0041] The term “aminoaryl” means an H₂N-aryl-group or radical whereinaryl has the meaning as defined above. The aminoaryl group is asubstituted aryl group or radical containing at least one substituentwhich is NH₂.

[0042] The term “carbocycle” means cycloalkyl as defined above.

[0043] The term “heteroatom” means a nitrogen, sulfur, or oxygen.

[0044] The term “heterocycle” means a heterocyclic radical which are 5-7atoms having 1-4 heteroatoms and are selected from: furan, pyrrole,thiophene, oxazole, isoxazole, thiazole, pyrazole, 1,2,3-triazole,1,2,4-triazole, tetrazole, pyridine, pyridazine, pyrimidine, pyrazine,tetrahydrofuran, tetrahydrothiophene, pyrrolidine, piperazine,piperidine, morpholine, thiomorpholine, oxolane, dioxane, sulfolane,unsubstituted or substituted by 1 to 2 substituents selected from alkylas defined above. For heterocycles containing sulfur, the oxidizedsulfur heterocycles containing SO or SO₂ groups are also included.

[0045] The term “benzoheterocyclic ring” (“fused heterocycle”) refers toa heterocycle that is adjoined at two consecutive positions with aphenyl ring or another heterocycle, such rings may include 2-, 3-, 4-,5-, 6-, 7-, or 8-quinolinyl, 1-, 3-, 4-, 5-, 6-, 7-, or 8-isoquinolinyl,2-, 3-, 4-, 5-, 6-, or 7-indolyl, 2-, 3-, 4-, 5-, 6-, or7-benzo[b]thienyl, 2-, 4-, 5-, 6-, or 7-benzoxazolyl, 2-, 4-, 5-, 6-, or7-benzimidazol, 2-, 4-, 5-, 6-, or 7-benzothiazolyl.

[0046] Some of the compounds of Formula I are capable of further formingpharmaceutically acceptable acid-addition and/or base salts. All ofthese forms are within the scope of the present invention.

[0047] Pharmaceutically acceptable acid addition salts of the compoundsof Formula I include salts derived from nontoxic inorganic acids such ashydrochloric, nitric, phosphoric, sulfuric, hydrobromic, hydriodic,hydrofluoric, phosphorous, and the like, as well as the salts derivedfrom nontoxic organic acids, such as aliphatic mono- and dicarboxylicacids, phenyl-substituted alkanoic acids, hydroxy alkanoic acids,alkanedioic acids, aromatic acids, aliphatic and aromatic sulfonicacids, etc. Such salts thus include sulfate, pyrosulfate, bisulfate,sulfite, bisulfite, nitrate, phosphate, monohydrogenphosphate,dihyrogenphosphate, metaphosphate, pyrophosphate, chloride, bromide,iodide, acetate, trifluoroacetate, propionate, caprylate, isobutyrate,oxalate, malonate, succinates suberate, sebacate, fumarate, maleate,mandelate, benzoate, chlorobenzoate, methylbenzoate, dinitrobenzoate,phthalate, benzenesulfonate, toluenesulfonate, phenylacetate, citrate,lactate, maleate, tartrate, methanesulfonate, and the like. Alsocontemplated are salts of amino acids such as arginate and the like andgluconate, galacturonate (see, for example, Berge S. M., et al.,“Pharmaceutical Salts,” Journal of Pharmaceutical Science, 1977;66:1-19.

[0048] The acid addition salt of said basic compounds are prepared bycontacting the free base form with a sufficient amount of the desiredacid to produce the salt in the conventional manner.

[0049] Pharmaceutically acceptable base addition salts are formed withmetals or amines, such as alkali and alkaline earth metals or organicamines. Examples of metals used as cations are sodium, potassium,magnesium, calcium, and the like. Examples of suitable amines areN,N′-dibenzylethylenediamine, chloroprocaine, choline, diethanolamine,dicyclohexylamine, ethylenediamine, N-methylglucamine, and procaine(see, for example, Berge, supra., 1977).

[0050] The base addition salts of said acidic compounds are prepared bycontacting the free acid form with a sufficient amount of the desiredbase to produce the salt in the conventional manner.

[0051] Certain of the compounds of the present invention can exist inunsolvated forms as well as solvated forms, including hydrated forms. Ingeneral, the solvated forms, including hydrated forms, are equivalent tounsolvated forms and are intended to be encompassed within the scope ofthe present invention.

[0052] Certain of the compounds of the present invention possess one ormore chiral centers and each center may exist in the R(D) or S(L)configuration. The present invention includes all enantiomeric andepimeric forms as well as the appropriate mixtures thereof.Configuration drawn is most preferred.

[0053] The compounds of the present invention can be prepared andadministered in a wide variety of oral and parenteral dosage forms.Thus, the compounds of the present invention can be administered byinjection, that is, intravenously, intramuscularly, intracutaneously,subcutaneously, intraduodenally, or intraperitoneally. Also, thecompounds of the present invention can be administered by inhalation,for example, intranasally. Additionally, the compounds of the presentinvention can be administered transdermally. It will be obvious to thoseskilled in the art that the following dosage forms may comprise as theactive component, either a compound of Formula I or a correspondingpharmaceutically acceptable salt of a compound of Formula I.

[0054] For preparing pharmaceutical compositions from the compounds ofthe present invention, pharmaceutically acceptable carriers can beeither solid or liquid. Solid form preparations include powders,tablets, pills, capsules, cachets, suppositories, and dispersiblegranules. A solid carrier can be one or more substances, which may alsoact as diluents, flavoring agents, binders, preservatives, tabletdisintegrating agents, or an encapsulating material.

[0055] In powders, the carrier is a finely divided solid, which is in amixture with the finely divided active component.

[0056] In tablets, the active component is mixed with the carrier havingthe necessary binding properties in suitable proportions and compactedin the shape and size desired.

[0057] The powders and tablets preferably contain from five or ten toabout seventy percent of the active compound. Suitable carriers aremagnesium carbonate, magnesium stearate, talc, sugar, lactose, pectin,dextrin, starch, gelatin, tragacanth, methylcellulose, sodiumcarboxymethylcellulose, a low melting wax, cocoa butter, and the like.The term “preparation” is intended to include the formulation of theactive compound with encapsulating material as a carrier providing acapsule in which the active component with or without other carriers, issurrounded by a carrier, which is thus in association with it.Similarly, cachets and lozenges are included. Tablets, powders,capsules, pills, cachets, and lozenges can be used as solid dosage formssuitable for oral administration.

[0058] For preparing suppositories, a low melting wax, such as a mixtureof fatty acid glycerides or cocoa butter, is first melted, and theactive component is dispersed homogeneously therein, as by stirring. Themolten homogenous mixture is then poured into convenient sized molds,allowed to cool, and thereby to solidify.

[0059] Liquid form preparations include solutions, suspensions, andemulsions, for example, water or water propylene glycol solutions. Forparenteral injection, liquid preparations can be formulated in solutionin aqueous polyethylene glycol solution.

[0060] Aqueous solutions suitable for oral use can be prepared bydissolving the active component in water and adding suitable colorants,flavors, stabilizing and thickening agents as desired.

[0061] Aqueous suspensions suitable for oral use can be made bydispersing the finely divided active component in water with viscousmaterial, such as natural or, synthetic gums, resins, methylcellulose,sodium carboxymethylcellulose, and other well-known suspending agents.

[0062] Also included are solid form preparations, which are intended tobe converted, shortly before use, to liquid form preparations for oraladministration. Such liquid forms include solutions, suspensions, andemulsions. These preparations may contain, in addition to the activecomponent, colorants, flavors, stabilizers, buffers, artificial andnatural sweeteners, dispersants, thickeners, solubilizing agents, andthe like.

[0063] The pharmaceutical preparation is preferably in unit dosage form.In such form the preparation is divided into unit doses containingappropriate quantities of the active component. The unit dosage form canbe a packaged preparation, the package containing discrete quantities ofpreparation, such as packeted tablets, capsules, and powders in vials orampoules. Also, the unit dosage form can be a capsule, tablet, cachet,or lozenge itself or it can be the appropriate number of any of these inpackaged form.

[0064] The quantity of active component in a unit dose preparation maybe varied or adjusted from 0.1 mg to 100 mg preferably 0.5 mg to 100 mgaccording to the particular application and the potency of the activecomponent. The composition can, if desired, also contain othercompatible therapeutic agents.

[0065] In therapeutic use as antagonists of a virus, as agents for thetreatment of infections caused by a virus or as agents for the treatmentof diseases due to a virus, the compounds utilized in the pharmaceuticalmethod of this invention are administered at the initial dosage of about0.01 mg to about 100 mg/kg daily. A daily dose range of about 0.01-mg toabout 10 mg/kg is preferred. The dosages, however, may be varieddepending upon the requirements of the patient, the severity of thecondition being treated, the compound being employed. Determination ofthe proper dosage for a particular situation is within the skill of theart. Generally, treatment is initiated with smaller dosages, which areless than the optimum dose of the compound. Thereafter, the dosage isincreased by small increments until the optimum effect under thecircumstances is reached. For convenience, the total daily dosage may bedivided and administered in portions during the day, if desired.

[0066] General Procedure 1 (for Singleton Synthesis):

[0067] Reductive Amination of Aryl Amines with Aldehydes or Ketones.

[0068] Reagent 2 (1 eq.) was taken in a solvent (dichloromethane,1,2-dichloroethane or tetrahydrofuran or diethyl ether) and to itreagent 1 (1 to 1.2 eq.) was added. To this solution cooled at 0° C. wasadded a reducing agent (sodium cyanoborohydride or sodiumtriacetoxyborohydride) (1 to 2 eq.). To it a drop of acetic acid wasadded and kept under stirring at room temperature for 6 to 24 hours. Theexcess hydride was quenched by adding methanol. The reaction mixture wasdiluted with ethyl acetate and washed with saturated ammonium chloridesolution, aqueous sodium bisulfite and brine; dried over anhydrousmagnesium sulfuate or sodium sulphate. Organic layer was concentratedand crude product was purified by flash silica gel chromatography toafford the final product. The products were characterized by spectraldata. The compounds synthesized using this procedure are shown in Table4.

[0069] General Procedure 2 for Multiple, Simultaneous Solution PhaseSynthesis (Combinatorial Chemistry Synthesis):

[0070] To a 2-dram glass vial were added, by Tecan liquid handlingrobot, a solution of reagent 2 (0.05 mmol) in trimethyl orthoformate(0.2 ml) followed by reagent 1 (0.05 mmol) in trimethyl orthoformate(0.2 ml). The vial was capped and the reaction mixture was shaken atroom temperature for 18 hours (overnight), then concentrated to dryness.To each vial was added, by Tecan™ liquid handling robot,1,2-dichloroethane (1 ml). Solid sodium triacetoxyborohydride (˜23 mg)was added manually to each vial. A a solution of acetic acid (0.05 mmol)in dichloroethane (0.05 ml) was added to each vial by Tecan™ liquidhandling robot. The vial was again capped and the reaction mixture wasshaken at room temperature for 18 hours (overnight). To the reactionmixture was added, by Tecan liquid handling robot, methanol (1 ml). Thereaction mixture was then transferred, by Tecan liquid handling robot,to be prewashed (That is washed with methanol (2 ml) and dichloroethane(1 ml)) BAKERBOND spe™ Aromatic Sulfonic Acid (SO₃H) disposableExtraction Columns. The columns were allowed to drain and then washedwith methanol (2×1 ml) these solvents were discarded. The desiredproduct was eluted from the column using a solution of 2M ammonia inmethanol (3×1 ml) and concentrated to dryness in a tared 2-dram vial.The product was analyzed by LCMS (liquid chromotography mass spec).

[0071] General Procedure 3 for Multiple, Simultaneous Solution PhaseSynthesis (Combinatorial Chemistry Synthesis):

[0072] To a 2-dram glass vial were added, by Tecan™ liquid handlingrobot, a solution of reagent 2 (0.05 mmol) in N,N-dimethylformamide (0.1ml) followed by reagent 1 (0.05 mmol) in N,N-dimethylformamide (0.1 ml).Each vial was treated with trimethylorthoformate (0.2 ml) by Tecan™liquid handling robot. The vial was capped and the reaction mixture wasshaken at room temperature for 18 hours (overnight), then concentratedto dryness. To each vial was added, by Tecan™ liquid handling robot,1,2-dichloroethane (1 ml). Solid sodium triacetoxyborohydride (˜23 mg)was added manually to each vial. A solution of acetic acid (0.05 mmol)in 1,2-dichloroethane (0.05 ml) was added to each vial by Tecan™ liquidhandling robot. The vial was again capped and the reaction mixture wasshaken at room temperature for 18 hours (overnight). To the reactionmixture was added, by Tecan™ liquid handling robot, methanol (1 ml). Thereaction mixture was then transferred, by Tecan™ liquid handling robot,to be prewashed (That is washed with methanol (2 ml) and1,2-dichloroethane (1 ml)) BAKERBOND spe™ Aromatic Sulfonic Acid (SO₃H)disposable Extraction Columns. The columns were allowed to drain andthen washed with methanol (2×1 ml) these solvents were discarded. Thedesired product was eluted from the column using a solution of 2Mammonia in methanol (3×1 ml) and concentrated to dryness in a tared2-dram vial. The product was analyzed by LCMS (liquid chromatographymass spec).

[0073] General Procedure 4 for Multiple, Simultaneous Solution PhaseSynthesis (Combinatorial Chemistry Synthesis):

[0074] To a 2-dram glass vial were added, by Tecan™ liquid handlingrobot, a solution of reagent 2 (0.05 mmol) in methanol (0.2 ml) followedby reagent 1 (0.2 mmol) in methanol (0.2 ml). To each vial was added, byTecan™ liquid handling robot, a 1N solution of sodium cyanoborohydridein methanol (0.2 ml) and a 10% acetic acid in methanol (0.05 ml)solution. The vial was capped and the reaction mixture was shaken atroom temperature for 18 hours (overnight), then concentrated to dryness.The vial was again capped and the reaction mixture was shaken at roomtemperature for 18 hours (overnight). To the reaction mixture was added,by Tecan™ liquid handling robot, methanol (1 ml). The reaction mixturewas then transferred, by Tecan™ liquid handling robot, to be prewashed(That is washed with methanol (2 ml) and 1,2-dichloroethane (1 ml))BAKERBOND spe™ Aromatic Sulfonic Acid (SO₃H) disposable ExtractionColumns. The columns were allowed to drain and then washed with methanol(2×1 ml) these solvents were discarded. The desired product was elutedfrom the column using a solution of 2M ammonia in methanol (3×1 ml) andconcentrated to dryness in a tared 2-dram vial. The product was analyzedby LCMS (liquid chromatography mass spec).

[0075] General Procedure 5 for Multiple, Simultaneous Solution PhaseSynthesis (Combinatorial Chemistry Synthesis):

[0076] To a 2-dram glass vial were added, by Tecan™ liquid handlingrobot, a solution of reagent 2 (0.05 mmol) in 1,2-dichloroethane (0.2ml) followed by reagent 1 (0.15 mmol) in 1,2-dichloroethane (0.1 ml). Toeach vial solid sodium triacetoxyborohydride (˜25 mg) was addedmanually. A solution of acetic acid (0.05 mmol) in 1,2-dichloroethane(0.05 ml) was added to each vial by Tecan™ liquid handling robot. Thevial was capped and the reaction mixture was shaken at room temperaturefor 18 hours (overnight). To the reaction mixture was added, by Tecan™liquid handling robot, methanol (1 ml). The reaction mixture was thentransferred, by Tecan™ liquid handling robot, to be prewashed (washedwith methanol (2 ml) and 1,2-dichloroethane (1 ml)) BAKERBOND spe™Aromatic Sulfonic Acid (SO₃H) disposable Extraction Columns. The columnswere allowed to drain and then washed with methanol (2×1 ml) thesesolvents were discarded. The desired product was eluted from the columnusing a solution of 2M ammonia in methanol (3×1 ml) and concentrated todryness in a tared 2-dram vial. The product was analyzed by LCMS (liquidchromatography mass spec).

[0077] General Procedure 6 for Multiple, Simultaneous Solution PhaseSynthesis (Combinatorial Chemistry Synthesis):

[0078] To a 2-dram glass vial were added, by Tecan™ liquid handlingrobot, a solution of reagent 2 (0.05 mmol) in methanol (0.2 ml) followedby reagent 1 (0.15 mmol) in methanol (0.1 ml). To each vial was added a1N solution of sodium cyanoborohydride in methanol (0.1 ml) and a 10%acetic acid in methanol solution (0.05 ml). The vial was capped and thereaction mixture was shaken at room temperature for 18 hours(overnight). To the reaction mixture was added, by Tecan™ liquidhandling robot, methanol (1 ml). The reaction mixture was thentransferred, by Tecan™ liquid handling robot, to be prewashed (washedwith methanol (2 ml) and 1,2-dichloroethane (1 ml)) BAKERBOND spe™Aromatic Sulfonic Acid (SO₃H) disposable Extraction Columns. The columnswere allowed to drain and then washed with methanol (2×1 ml) thesesolvents were discarded. The desired product was eluted from the columnusing a solution of 2M ammonia in methanol (3×1 ml) and concentrated todryness in a tared 2-dram vial. The product was analyzed by LCMS (liquidchromatography mass spec).

[0079] General Procedure 7 for Multiple, Simultaneous Solution PhaseSynthesis (Combinatorial Chemistry Synthesis):

[0080] To a 2-dram glass vial were added, by Tecan™ liquid handlingrobot, a solution of reagent 2 (0.05 mmol) followed by reagent 1 inN,N-dimethylformamide (0.32 ml) or methanol (0.2 ml). The vials werethen concentrated overnight to dryness. Each vial was treated by Tecan™liquid handling robot with reagent 1 (0.15 mmol) in methanol (0.1 ml)and methanol (0.2 ml). To each vial was added a 1N solution of sodiumcyanoborohydride in methanol (0.1 ml) and a 10% acetic acid in methanolsolution (0.05 ml). The vial was capped and the reaction mixture wasshaken at room temperature for 18 hours (overnight). To the reactionmixture was added, by Tecan™ liquid handling robot, methanol (1 ml). Thereaction mixture was then transferred, by Tecan™ liquid handling robot,to be prewashed (washed with methanol (2 ml) and 1,2-dichloroethane (1ml)) BAKERBOND spe™ Aromatic Sulfonic Acid (SO₃H) disposable ExtractionColumns. The columns were allowed to drain and then washed with methanol(2×1 ml) these solvents were discarded. The desired product was elutedfrom the column using a solution of 2M ammonia in methanol (3×1 ml) andconcentrated to dryness in a tared 2-dram vial. The product was analyzedby LCMS (liquid chromatography mass spec).

[0081] Synthesis of Compound 450: To dibenzofuran-2-yl-amine (0.91 g, 5mmol) taken in dichloromethane (75 mL) was addedα,α′-dibromo-ortho-xylene (1.85 g, 7 mmol) followed by triethylamine(3.03 g, 30 mmol). The reaction was stirred at room temperature for 24hours. The solvents were evaporated and the residue was purified byflash silica gel chromatography to give the title compound (1.43 g).

[0082] Synthesis of Compound 451: To dibenzofuran-2-yl-amine (0.91 g, 5mmol) taken in dichloromethane (75 mL) was added phthaloyl dichloride(1.16 g, 6 mmol) followed by triethylamine (3.03 g, 30 mmol). Thereaction was stirred at room temperature for 5 minutes. The reaction wasquenched with sodium bicarbonate solution and the organic layer wasseparated. The crude product was purified by flash silica gelchromatography to give the title compound (0.51 g).

[0083] Synthesis of Compound 463: To compound 58 (0.25 g, 0.87 mmol)taken in tetrahydrofuran (10 mL) was added sodium hydride (60% inmineral oil, 0.035 g, 0.87 mmol). To it methyl iodide (0.25 g, 1.74mmol) was added. The reaction was stirred at room temperature for 24hours. The solvents were evaporated and the residue was purified byflash silica gel chromatography to give the title compound (0.18 g).

[0084] Deprotection of t-butyloxycarbonyl group: The general procedurefor the removal of tert-butyoxycarbonyl (Boc) group is as follows: Tothe compound taken a flask was added hydrochloric acid in an appropriatesolvent (dioxane, methanol, 1,2-dichloromethane and the reaction waskept under shaking for 5 to 18 hours. Removal of volatiles furnished thecorresponding product.

[0085] Reagents 1 are shown in Table 1. TABLE 1 Aldehydes/ketones(reagent 1) No. Reagent 1 (aldehydes/ketones) 1 o-tolualdehyde 2meta-tolualdehyde 3 para-tolualdehyde 4 2-fluorobenzaldehyde 53-fluorobenzaldehyde 6 4-fluorobenzaldehyde 7 4-tert-butylbenzaldehyde 8α,α,α-Trilfluoro-o-tolualdehyde 9 α,α,α-Trilfluoro-m-tolualdehyde 10α,α,α-Trilfluoro-p-tolualdehyde 11 o-anisaldehyde 12 m-anisaldehyde 13p-anisaldehyde 14 Salicylaldehyde 15 3-hydroxybenzaldehyde 164-hydroxybenzaldehyde 17 2-chlorobenzaldehyde 18 3-chlorobenzaldehyde 194-chlorobenzaldehyde 20 3-benzyloxybenzaldehyde 214-benzyloxybenzaldehyde 22 2,3-dimethoxybenzaldehyde 232,4-dimethoxybenzaldehyde 24 2,5-dimethoxybenzaldehyde 252,6-dimethoxybenzaldehyde 26 3,4-dimethoxybenzaldehyde 273,5-dimethoxybenzaldehyde 28 1,4-Benzodioxan-6-carboxaldehyde 292,4-dimethylbenzaldehyde 30 2,5-dimethylbenzaldehyde 312,3-difluorobenzaldehyde 32 2,4-difluorobenzaldehyde 332,5-difluorobenzaldehyde 34 2,6-difluorobenzaldehyde 353,4-difluorobenzaldehyde 35 3,5-difluorobenzaldehyde 372,3,4-trifluorobenzaldehyde 38 2,3,6-trifluorobenzaldehyde 393-fluoro-2-methylbenzaldehyde 40 3-fluoro-p-anisaldehyde 412-pyridinecarboxaldehyde 42 3-pyridinecarboxaldehyde 434-pyridinecarboxaldehyde 44 4-pyridinecarboxaldehyde N-oxide 456-methyl-2-pyridinecarboxaldehyde 46 3-furaldehyde 47 2-furaldehyde 485-chloro-2-thiophenecarboxaldehyde 49 3-thiophenecarboxaldehyde 502-thiophenecarboxaldehyde 51 pyrrole-2-carboxaldehyde 521-methyl-2-pyrrolecarboxaldehyde 53 1-naphthaldehyde 54 2-naphthaldehyde55 2-quinolinecarboxaldehyde 56 3-quinolinecarboxaldehyde 574-quinolinecarboxaldehyde 58 indole-3-carboxaldehyde 592-bromobenzaldehyde 60 2-chlorobenzaldehyde 61 2-ethoxybenzaldehyde 622-cyanobenzaldehyde 63 5-(2-chlorophenyl)furfural 645-(3-chlorophenyl)furfural 65 5-(4-chlorophenyl)furfural 662-thiazolecarboxaldehyde 67 2-imidazolecarboxaldehyde 684(5)-imidazolecaboxaldehyde 69 5-nitro-2-thiophenecarboxaldehyde 702-nitrobenzaldehyde 71 4-formyluracil 72 4-acetoxybenzaldehyde 734-(dimethylamino)benzaldehyde 74 1-acetyl-3-indolecarboxaldehyde 754-bromo-2-thiophenecarboxaldehyde 76 Piperonal 773-trifluoromethoxybenzaldehyde 78 4-chloro-3-nitro-benzaldehyde 79Benzaldehyde 80 3-benzyloxybenzaldehyde 81 3-phenoxybenzaldehyde 822-butanone 83 2-Pentanone 84 3-Methyl-2-butanone 85Tetrahydrothiophene-3-one 86 Tetrahydrothiopyran-4-one 87 Cycloheptanone88 Cyclooctanone 89 Cyclohexylmethylketone 90 4-Methyl-2-pentanone 913-Pentanone 92 3-Hexanone 93 4-Hydroxy-3-methyl-2-butanon 942-Methoxyphenylacetone 95 4-nitrobenzaldehyde 964-(methylthio)benzaldehyde 97 Propionaldehyde 98 Isovaleraldehyde 993-(methylthio)propionaklehyde 100 1-phenyl-2-pentanone 101 Acetone 102Cyclopropyl methyl ketone 103 Cyclohexanone 104n-tert-butoxycarbonyl-4-piperidone 105 3,3,5,5-tetramethylcyclohexanone106 1-decalone 107 4-cyclohexylcyclohexanone 108 2-norbornanone 1094-tert-butylcyclohexanone 110 Cyclopentanone 111 2-adamantanone 112Bicyclo[3,2,1]octan-2-one 113 1,1-dioxo-tetrahydro-thiopyran-4-one

[0086] Reagent 2 (amines) used in the above general procedures are shownin Table 2: TABLE 2 No. Reagent 2 (amines) 1Dibenzofuran-2-yl-methyl-amine 2 8-fluoro-dibenzofuran-2-yl-amine 38-chloro-dibenzofuran-2-yl-amine 4 8-amino-dibenzofuran-2-ol 53-methoxy-diebenzofuran-2-yl-amine 6 9H-Fluoren-3-yl-amine 79H-Fluorene-2-yl-amine 8 Dibenzofuran-4-yl-amine 9Benzo[4,5]furo[2,3-H]pyridin-3-yl-amine 10 9-Ethyl-9H-carbazol-3-ylamine11 3-Amino-carbazole-9-carboxylic acid tert-butyl ester 12Dibenzofuran-2-yl-methyl-amine 13 Dibenzofuran-2-yl-dimethyl-amine 14Dibenzothiophene-2-yl-amine 15 Dibenzothiophene-3-yl-amine 166-Amino-1,2,3,4-tetrahydro-carbazole-9-carboxylic acid tert-butyl ester17 Dibenzo[1,4]dioxin-2-yl-amine 18 Phenoxanthiin-3-yl-amine 1910-Oxa-9-thia-1-aza-anthracen-3-yl-amine 2010H-Benzo-b]pyrido[2,3-e][1,4]oxazin-3-ylamine acetic acid, tert-butylester 21 Anthracen-2-yl-amine 2210,111-Dihydro-5H-diebnzo[b,f]azepin-3-yl-amine 236,7,8,9-Tetrahydro-5H-carbazol-3-yl-amine 24 7-Amino-1-aza-phenoxathiin

[0087] The compounds of Formula I include:

[0088] 1 (1-Cyclopropyl-ethyl)-(2-methoxy-dibenzofuran-3-yl)-amine

[0089] 2 Cyclopentyl-(9H-fluoren-2-yl)-amine

[0090] 3 (1-Cyclopropyl-ethyl)-(9H-fluoren-2-yl)-amine

[0091] 4 N³-Cyclopentyl-N²,N²-dimethyl-9H-fluorene-2,3-diamine

[0092] 5 Isopropyl-(2-methoxy-dibenzofuran-3-yl)-amine

[0093] 6 (2-Methoxy-dibenzofuran-3-yl)-(tetrahydro-thiopyran-4-yl)-amine

[0094] 7 Cycloheptyl-(2-methoxy-dibenzofuran-3-yl)-amine

[0095] 8 (1-Ethyl-propyl)-(2-methoxy-dibenzofuran-3-yl)-amine

[0096] 9 sec-Butyl-(2-methoxy-dibenzofuran-3-yl)-amine

[0097] 10 N²,N²-Dimethyl-N³-piperidin-4-yl-9H-fluorene-2,3-diamine

[0098] 11 N³-(1-Benzyl-butyl)-N²,N²-dimethyl-9H-fluorene-2,3-diamine

[0099] 12 (9H-Fluoren-2-yl)-piperidin-4-yl-amine

[0100] 13 (1-Benzyl-butyl)-(9H-fluoren-2-yl)-amine

[0101] 14 sec-Butyl-(9H-fluoren-2-yl)-amine

[0102] 15(1,1-Dioxo-hexahydro-thiopyran-4-yl)-(2-methoxy-dibenzofuran-3-yl)-amine

[0103] 16 Dibenzofuran-2-yl-(3,3,5,5-tetramethyl-cyclohexyl)-amine

[0104] 17 (Decahydro-naphthalen-1-yl)-dibenzofuran-2-yl-amine

[0105] 18 Adamantan-2-yl-dibenzofuran-2-yl-amine

[0106] 19 Bicyclohexyl-4-yl-dibenzofuran-2-yl-amine

[0107] 20 Bicyclo[2.2.1]hept-2-yl-dibenzofuran-2-yl-amine

[0108] 21 (4-tert-Butyl-cyclohexyl)-dibenzofuran-2-yl-amine

[0109] 22 Bicyclo[3.2.1]oct-2-yl-dibenzofuran-2-yl-amine

[0110] 23 Cyclopentyl-dibenzofuran-2-yl-amine

[0111] 24 Cyclohexyl-(2-methoxy-dibenzofuran-3-yl)-amine

[0112] 25 Cyclohexyl-(9H-fluoren-2-yl)-amine

[0113] 26 Dibenzofuran-2-yl-bis-(3-methylsulfanyl-propyl)-amine

[0114] 27 Dibenzofuran-2-yl-bis-(3-methyl-butyl)-amine

[0115] 28 Dibenzofuran-2-yl-dipropyl-amine

[0116] 29N³-(1,1-Dioxo-hexahydro-thiopyran-4-yl)-N²,N²-dimethyl-9H-fluorene-2,3-diamine

[0117] 30 N³-Isopropyl-N²,N²-dimethyl-9H-fluorene-2,3-diamine

[0118] 31N²,N²-Dimethyl-N³-(tetrahydro-thiopyran-4-yl)-9H-fluorene-2,3-diamine

[0119] 32 N³-Cyclohexyl-N²,N²-dimethyl-9H-fluorene-2,3-diamine

[0120] 33 N³-Cycloheptyl-N²,N²-dimethyl-9H-fluorene-2,3-diamine

[0121] 34 N³-(1-Ethyl-propyl)-N²,N²-dimethyl-9H-fluorene-2,3-diamine

[0122] 35N³-(1-Cyclopropyl-ethyl)-N²,N²-dimethyl-9H-fluorene-2,3-diamine

[0123] 36 N³-sec-Butyl-N²,N²-dimethyl-9H-fluorene-2,3-diamine

[0124] 37 (9H-Fluoren-2-yl)-isopropyl-amine

[0125] 38 (9H-Fluoren-2-yl)-(tetrahydro-thiopyran-4-yl)-amine

[0126] 39 Cycloheptyl-(9H-fluoren-2-yl)-amine

[0127] 40 Dibenzofuran-2-yl-(1,1-dioxo-hexahydro-thiopyran-4-yl)-amine

[0128] 41 Dibenzofuran-2-yl-piperidin-4-yl-amine

[0129] 42 Dibenzofuran-2-yl-isopropyl-amine

[0130] 43 Cyclohexyl-dibenzofuran-2-yl-amine

[0131] 44 (1-Cyclopropyl-ethyl)-dibenzofuran-2-yl-amine

[0132] 45 Dibenzofuran-3-yl-(1,1-dioxo-hexahydro-thiopyran-4-yl)-amine

[0133] 46 Dibenzofuran-3-yl-piperidin-4-yl-amine

[0134] 47 Dibenzofuran-3-yl-isopropyl-amine

[0135] 48 Dibenzofuran-3-yl-(tetrahydro-thiopyran-4-yl)-amine

[0136] 49 Cyclohexyl-dibenzofuran-3-yl-amine

[0137] 50 Cycloheptyl-dibenzofuran-3-yl-amine

[0138] 51 (4-Chloro-benzyl)-dibenzofuran-2-yl-amine

[0139] 52 (4-Chloro-3-nitro-benzyl)-dibenzofuran-2-yl-amine

[0140] 53 Dibenzofuran-2-yl-(3-trifluoromethoxy-benzyl)-amine

[0141] 54 Benzo[1,3]dioxol-5-ylmethyl-dibenzofuran-2-yl-amine

[0142] 55Dibenzofuran-2-yl-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-amine

[0143] 56 Dibenzofuran-2-yl-(3,5-dimethoxy-benzyl)-amine

[0144] 57 Dibenzofuran-2-yl-(4-trifluoromethyl-benzyl)-amine

[0145] 58 Dibenzofuran-2-yl-(2-methyl-benzyl)-amine

[0146] 59 Dibenzofuran-2-yl-thiophen-3-ylmethyl-amine

[0147] 60 Dibenzofuran-2-yl-(4-nitro-benzyl)-amine

[0148] 61 Dibenzofuran-2-yl-(4-methylsulfanyl-benzyl)-amine

[0149] 62 Dibenzofuran-2-yl-(4-methyl-benzyl)-amine

[0150] 63 Benzyl-dibenzofuran-2-yl-amine

[0151] 64 (3-Benzyloxy-benzyl)-dibenzofuran-2-yl-amine

[0152] 65 (1-Benzyl-butyl)-dibenzofuran-2-yl-amine

[0153] 66 Dibenzofuran-2-yl-[2-(2-methoxy-phenyl)-1-methyl-ethyl]-amine

[0154] 67 3-(Dibenzofuran-2-ylamino)-2-methyl-butan-1-ol

[0155] 68 Dibenzofuran-2-yl-(1-ethyl-butyl)-amine

[0156] 69 Dibenzofuran-2-yl-(1-ethyl-propyl)-amine

[0157] 70 Dibenzofuran-2-yl-(1,3-dimethyl-butyl)-amine

[0158] 71 (1-Cyclohexyl-ethyl)-dibenzofuran-2-yl-amine

[0159] 72 Cyclooctyl-dibenzofuran-2-yl-amine

[0160] 73 Cycloheptyl-dibenzofuran-2-yl-amine

[0161] 74 Dibenzofuran-2-yl-(tetrahydro-thiopyran-4-yl)-amine

[0162] 75 Dibenzofuran-2-yl-(tetrahydro-thiophen-3-yl)-amine

[0163] 76 Dibenzofuran-2-yl-(1,2-dimethyl-propyl)-amine

[0164] 77 Dibenzofuran-2-yl-(1-methyl-butyl)-amine

[0165] 78 sec-Butyl-dibenzofuran-2-yl-amine

[0166] 79 Benzofurp[3,2-b]pyridin-8-yl-(2-fluoro-benzyl)-amine

[0167] 80 Benzofuro[3,3-b]pyridin-8-yl-pyridin4-ylmethyl-amine

[0168] 81 Benzofuro[3,2-b]pyridin-8-yl-(2-methyl-benzyl)-amine

[0169] 82 N-(2-Fluoro-benzyl)-N′-methyl-dibenzofuran-2,8-diamine

[0170] 83 N-Methyl-N′-quinolin-4-ylmethyl-dibenzofuran-2,8-diamine

[0171] 84 N-Methyl-N′-naphthanlen-1-ylmethyl-dibenzofuran-2,8-diamine

[0172] 85 N-(4-Methanesulfonyl-benzyl)-N′-methyl-dibezofuran-2,8-diamine

[0173] 86 N-Methyl-N′-pyridin-4-ylmethyl-dibenzofuran-2,8-diamine

[0174] 87 N-Methyl-N′-(2-methyl-benzyl)-dibenzofuran-2,8-diamine

[0175] 88 Naphthanlen-1-ylmethyl-(10H-phenothiazin-2-yl)-amine

[0176] 89 (4-Methanesulfonyl-benzyl)-(10H-phenothiazin-2-yl)-amine

[0177] 90(3-Fluoro-2-methyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen-6-yl)-amine

[0178] 91(2-Fluoro-2-methyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen-6-yl)-amine

[0179] 92 (10-Oxa-9-thia-1-aza-anthracen-6-yl)-qinolin-4-ylmethyl-amine

[0180] 93Naphthalene-1-ylmethyl-(10-oxa-9-thia-1-aza-anthracen-6-yl)-amine

[0181] 94(4-Methanesulfonyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen-6-yl)-amine

[0182] 95 (10-Oxa-9-thia-1-aza-anthracen-6-yl)-pyridin-4-ylmethyl-amine

[0183] 96 (2-Methyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen-6-yl)-amine

[0184] 97 Anthracen-2-yl-quinolin-4-ylmethyl-amine

[0185] 98 Anthracen-2-yl-(4-methanesulfonyl-benzyl)-amine

[0186] 99 Anthracen-2-yl-pyridin-4-ylmethyl-amine

[0187] 100 Anthracen-2-yl-(2-methyl-benzyl)-amine

[0188] 101 Dibenzo[b,e][1,4]-dioxin-2-yl-(2-fluoro-benzyl)-amine

[0189] 102 Dibenzo[b,e][1,4]dioxin-2-yl-(2-fluoro-benzyl)-amine

[0190] 103 Dibenzo[b,e][1,4]fioxin-2-yl-quinolin-4-ylmethyl-amine

[0191] 104 Dibenzo[b,e][1,4]fioxin-2-yl-naphthalen-1-ylmethyl-amine

[0192] 105 Dibenzo[b,e][1,4]fioxin-2-yl-(4-methanesulfonyl-benzyl)-amine

[0193] 106 Dibenzo[b,e][1,4]fioxin-2-yl-pyridin-4-ylmethyl-amine

[0194] 107 8-(3-Fluoro-2-methyl-benzylamino)-dibenzofuran-2-ol

[0195] 108 8-(2-Fluoro-benzylamino)-dibenzofuran2-ol

[0196] 109 8-(4-Methanesulfonyl-benzylamino)-dibenzofuran-2-ol

[0197] 110 8-[(Pyridin-4-ylmethyl)-amino]-dibenzofuran-2-ol

[0198] 111 8-(2-Methyl-benzylamino)-dibenzofuran-2-ol

[0199] 112 (8-Chloro-dibenzofuran-2-yl)-(2-fluoro-benzyl)-amine

[0200] 113 8-Chloro-dibenzofuran-2-yl)-naphthalen-1-ylmethyl-amine

[0201] 114 8-Chloro-dibenzofuran-2-yl)-(4-methanesulfonyl-benzyl)-amine

[0202] 115(4-Methanesulfonyl-benzyl)-(6,7,8,9-tetrahydro-5H-carbazol-3-yl)-amine

[0203] 116Pyridin-4-ylmethyl-(6,7,8,9-tetrahydro-5H-carbazol-3-yl)-amine

[0204] 117 Benzofuro[3,2-b]pyridin-8-yl-(3-fluoro-2-methyl-benzyl)-amine

[0205] 118 Dibenzofuran-2-yl-quinolin-4-ylmethyl-amine

[0206] 119 Dibenzofuran-2-yl-quinolin-2-ylmethyl-amine

[0207] 120 (4-Dimethylamino-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0208] 121 Dibenzofuran-2-yl-(4-dimethylamino-benzyl)-amine

[0209] 122 Dibnzofuran-2-yl-(5-nitro-thiophen-2-ylmethyl)-amine

[0210] 123 Dibenzofuran-2-yl-thiazol-2-ylmethyl-amine

[0211] 124 Benzyl-(8-fluoro-dibenzofuran-2-yl)-amine

[0212] 125 N-(-3-Methoxybenzyl)-N′-methyl-dibenzofuran-2,8-diamine

[0213] 126 N-(3,5-Dimethoxy-benzyl)-N′-methyl-dibenzofuran-2,8-diamine

[0214] 127 N-(4-tert-Butyl-benzyl)-N′-methyl-dibenzofuran-2,8-diamine

[0215] 128 N-Benzyl-N′-methyl-dibenzofuran-2,8-diamine

[0216] 1292-[(8-Methylamino-dibenzofuran-2-ylamino)-methyl]-benzonitrile

[0217] 130 (4-Methoxy-benzyl)-phenoxathiin-3-yl-amine

[0218] 131 (8-Chloro-dibenzofuran-2-yl)-(3-methoxy-benzyl)-amine

[0219] 132 (3-Methoxy-benzyl)-phenoxathiin-3-yl-amine

[0220] 133 (3,5-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine

[0221] 134 (3-Fluoro-4-methoxy-benzyl)-phenoxathiin-3-yl-amine

[0222] 135 (4-tert-Butyl-benzyl)-phenoxathiin-3-yl-amine

[0223] 136 Benzyl-phenoxathiin-3-yl-amine

[0224] 137 (2-Ethoxy-benzyl)-phenoxathiin-3-yl-amine

[0225] 138 (8-Chloro-dibenzofuran-2-yl)-(3,5-dimethoxy-benzyl)-amine

[0226] 139(8-Chloro-dibenzofuran-2-yl)-(3-fluoro-4-methoxy-benzyl)-amine

[0227] 140 Benzyl-(8-chloro-dibenzofuran-2-yl)-amine

[0228] 141 (9H-Fluoren-2-yl)-(4-methoxy-benzyl)-amine

[0229] 142 (8-Chloro-dibenzofuran-2-yl)-thiazol-2-ylmethyl-amine

[0230] 143 (9H-Fluoren-2-yl)-(3-methoxy-benzyl)-amine

[0231] 144 (3,5-Dimethoxy-benzyl)-(9H-fluoren-2-yl)-amine

[0232] 145 (9H-Fluoren-2-yl)-(3-fluoro-4-methoxy-benzyl)-amine

[0233] 146 (4-tert-Butyl-benzyl)-(9H-fluoren-2-yl)-amine

[0234] 147 Benzyl-(9H-fluoren-2-yl)-amine

[0235] 148 (9H-Fluoren-2-yl)-thiazol-2-ylmethyl-amine

[0236] 149 (2-Ethoxy-benzyl)-(9H-fluoren2-yl-amine

[0237] 150 Dibenzofuran-4-yl-(4-methoxy-benzyl)-amine

[0238] 151 2-[(8-Chloro-dibenzofuran-2-ylamino)-methyl]-benzonitrile

[0239] 152 Dibenzofuran-4-yl-(3-methoxy-benzyl)-amine

[0240] 153 Dibenzofuran-4-yl-(3,5-dimethoxy-benzyl)-amine

[0241] 154 Dibenzofuran-4-yl-(3-fluoro-4-methoxy-benzyl)-amine

[0242] 155 (4-tert-Butyl-benzyl)-dibenzofuran-4-yl-amine

[0243] 156 Dibenzofuran-4-yl-(2-ethoxy-benzyl)-amine

[0244] 157 N-(4-Methoxy-benzyl)-N′-methyl-dibenzofuran-2,8-diamine

[0245] 158 (8-Chloro-dibenzofuran-2-yl)(4-methoxy-benzyl)-amine

[0246] 159 (8-Chloro-dibenzofuran-2-yl)-(2-ethoxy-benzyl)-amine

[0247] 160 Dibenzofuran-4yl-(2,4-dimethyl-benzyl)-amine

[0248] 161 N-Methyl-N′-thiophen-3-ylmethyl-dibenzofuran-2,8-diamine

[0249] 162 N-Methyl-N′-pyridin-2-ylmethyl-dibenzofuran-2,8-diamine

[0250] 163 (2-Bromo-benzyl)-phenoxathiin-3-yl-amine

[0251] 164 Phenoxathiin-3-yl-quinolin-4-ylmethyl-amine

[0252] 165 Phenoxathiin-3-yl-thiophen-3-ylmethyl-amine

[0253] 166 (3-Methyl-pyridin-2-ylmethyl)-phenoxathiin-3-yl-amine

[0254] 167 Phenoxathiin-3-yl-pyridin-3-ylmethyl-amine

[0255] 168 Phenoxathiin-3-yl-pyridin-2-ylmethyl-amine

[0256] 169 (8-Chloro-dibenzofuran-2-yl)-thiophen-3-ylmethyl-amine

[0257] 170 (2-Bromo-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine

[0258] 171(8-Chloro-dibenzofuran-2-yl)-(3-methyl-pyridin-2-ylmethyl)-amine

[0259] 172 (9-Ethyl-9H-carbazol-3-yl)-thiophen-3-ylmethyl-amine

[0260] 173(5-Chloro-thiophen-2-ylmethyl)-(9-ethyl-9H-carbazol-3-yl)-amine

[0261] 174 (9-Ethyl-9H-carbazol-3-yl)-pyridin-3-ylmethyl-amine

[0262] 175 (2-Bromo-benzyl)-(9H-fluoren-2-yl)-amine

[0263] 176 (8-Chloro-dibenzofuran-2-yl)-pyridin-4-ylmethyl-amine

[0264] 177 (9H-Fluoren-2-yl)-quinolin-2-ylmethyl-amine

[0265] 178 (9H-Fluoren-2-yl)-thiophen-3-ylmethyl-amine

[0266] 179 (9H-Fluoren-2-yl)-(3-methyl-pyridin-2-ylmethyl)-amine

[0267] 180 (9H-Fluoren-2-yl)-pyridin-4-ylmethyl-amine

[0268] 181 (9H-Fluoren-2-yl)-pyridin-3-ylmethyl-amine

[0269] 182 (9H-Fluoren-2-yl)-pyridin-2-ylmethyl-amine

[0270] 183 (8-Chloro-dibenzofuran-2-yl)-pyridin-3-ylmethyl-amine

[0271] 184 Dibenzofuran-4-yl-quinolin-4-ylmethyl-amine

[0272] 185 Dibenzofuran-4-yl-quinolin-2-ylmethyl-amine

[0273] 186 Dibenzofuran-4-yl-thiophen-3-ylmethyl-amine

[0274] 187 Dibenzofuran-4-yl-(3-methyl-pyridin-2-ylmethyl)-amine

[0275] 188 Dibenzofuran-4-yl-pyridin-4-ylmethyl-amine

[0276] 189 Dibenzofuran-4-yl-pyridin-3-ylmethyl-amine

[0277] 190 Dibenzofuran-4-yl-pyridin-2-ylmethyl-amine

[0278] 191 (2-Bromo-benzyl)-(8-chloro-dibenzofuran-2-yl)-amine

[0279] 192 (8-Chloro-dibenzofuran-2-yl)-pyridin-2-ylmethyl-amine

[0280] 193 N-Methyl-N′-(2,3,6-trifluoro-benzyl)-dibenzofuran-2,8-diamine

[0281] 194 N-Methyl-N′-(2,3,4-trifluoro-benzyl)-dibenzofuran-2,8-diamine

[0282] 195 N-(2,6-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-diamine

[0283] 196 N-(2,5-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-diamine

[0284] 197 N-(2,4-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-diamine

[0285] 198 N-(2,3-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-diamine

[0286] 199 N-(2,5-Dimethyl-benzyl)-N′-methyl-dibenzofuran-2,8-diamine

[0287] 200 N-(2,4-Dimethyl-benzyl)-N′-methyl-dibenzofuran-2,8-diamine

[0288] 201N-(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-N′-methyl-dibenzofuran-2,8-diamine

[0289] 202 (3-Fluoro-2-methyl-benzyl)-phenoxathiin-3-yl-amine

[0290] 203 (8-Chloro-dibenzofuran-2-yl)-(2,3,6-trifluoro-benzyl)-amine

[0291] 204 Phenoxathiin-3-yl-(2,3,6-trifluoro-benzyl)-amine

[0292] 205 Phenoxathiin-3-yl-(2,3,4-trifluoro-benzyl)-amine

[0293] 206 (2,6-Difluoro-benzyl)-phenoxathiin-3-yl-amine

[0294] 207 (2,5-Difluoro-benzyl)-phenoxathiin-3-yl-amine

[0295] 208 (2,4-Difluoro-benzyl)-phenoxathiin-3-yl-amine

[0296] 209 (2,3-Difluoro-benzyl)-phenoxathiin-3-yl-amine

[0297] 210 (2,4-Dimethyl-benzyl)-phenoxathiin-3-yl-amine

[0298] 211(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-phenoxathiin-3-yl-amine

[0299] 212 Benzo[b]thiophen-5-yl-(3-fluoro-2-methyl-benzyl)-amine

[0300] 213 (8-Chloro-dibenzofuran-2-yl)-(2,3,4-trifluoro-benzyl)-amine

[0301] 214 (8-Chloro-dibenzofuran-2-yl)-(2,6-difluoro-benzyl)-amine

[0302] 215 (8-Chloro-dibenzofuran-2-yl)-(2,5-difluoro-benzyl)-amine

[0303] 216 (8-Chloro-dibenzofuran-2-yl)-(2,4-difluoro-benzyl)-amine

[0304] 217 (9-Ethyl-9H-carbazol-3-yl)-(3-fluoro-2-methyl-benzyl)-amine

[0305] 218 (8-Chloro-dibenzofuran-2-yl)-(2,3-difluoro-benzyl)-amine

[0306] 219 (9-Ethyl-9H-carbazol-3-yl)-(2,3,6-trifluoro-benzyl)-amine

[0307] 220 (9-Ethyl-9H-carbazol-3-yl)-(2,3,4-trifluoro-benzyl)-amine

[0308] 221 (2,6-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine

[0309] 222 (2,5-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine

[0310] 223 (2,4-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine

[0311] 224 (2,3-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine

[0312] 225 (2,5-Dimethyl-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine

[0313] 226 (2,4-Dimethyl-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine

[0314] 227(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-(9-ethyl-9H-carbazol-3-yl)-amine

[0315] 228 (9H-Fluoren-2-yl)-(3-fluoro-2-methyl-benzyl)-amine

[0316] 229 (8-Chloro-dibenzofuran-2-yl)-(2,5-dimethyl-benzyl)-amine

[0317] 230 (9H-Fluoren-2-yl)-(2,3,6-trifluoro-benzyl)-amine

[0318] 231 (9H-Fluoren-2-yl)-(2,3,4-trifluoro-benzyl)-amine

[0319] 232 (2,5-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine

[0320] 233 (2,4-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine

[0321] 234 (2,3-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine

[0322] 235 (2,5-Dimethyl-benzyl)-(9H-fluoren-2-yl)-amine

[0323] 236 (2,4-Dimethyl-benzyl)-(9H-fluoren-2-yl)-amine

[0324] 237(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-(9H-fluoren-2-yl)-amine

[0325] 238 (8-Chloro-dibenzofuran-2-yl)-(2,4-dimethyl-benzyl)-amine

[0326] 239 Dibenzofuran-4-yl-(2,5-dimethyl-benzyl)-amine

[0327] 240 Dibenzofuran-4-yl-(3-fluoro-2-methyl-benzyl)-amine

[0328] 241N-(3-Fluoro-2-methyl-benzyl)-N′-methyl-dibenzofuran-2,8-diamine

[0329] 242 (8-Chloro-dibenzofuran-2-yl)-(3-fluoro-2-methyl-benzyl)-amine

[0330] 243(8-Chloro-dibenzofuran-2-yl)-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-amine

[0331] 244 (2,5-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine

[0332] 245 (2,3-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine

[0333] 246 (2-Chloro-benzyl)-phenoxathiin-3-yl-amine

[0334] 247 (2-Methoxy-benzyl)-phenoxathiin-3-yl-amine

[0335] 248 (2-Methyl-benzyl)-phenoxathiin-3-yl-amine

[0336] 249 Anthracen-2-yl-(2-chloro-benzyl)-amine

[0337] 250 Anthracen-2-yl-(2-fluoro-benzyl)-amine

[0338] 251 Dibenzo[1,4]dioxin-2-yl-(2,3-dimethoxy-benzyl)-amine

[0339] 252 (2-Chloro-benzyl)-dibenzo[1,4]dioxin-2-yl-amine

[0340] 253 2-(Dibenzo[1,4]dioxin-2-ylaminomethyl)-phenol

[0341] 254 Dibenzo[1,4]dioxin-2-yl-(2-methoxy-benzyl)-amine

[0342] 255 2-[(9-Ethyl-9H-carbazol-3-ylamino)-methyl]-phenol

[0343] 256 (9-Ethyl-9H-carbazol-3-yl)-(2-fluoro-benzyl)-amine

[0344] 257 (9-Ethyl-9H-carbazol-3-yl)-(2-methyl-benzyl)-amine

[0345] 258 (2-Chloro-benzyl)-(9H-fluoren-2-yl)-amine

[0346] 259 2-[(9H-Fluoren-2-ylamino)-methyl]-phenol

[0347] 260 (9H-Fluoren-2-yl)-(2-methoxy-benzyl)-amine

[0348] 261 (9H-Fluoren-2-yl)-(2-trifluoromethyl-benzyl)-amine

[0349] 262 (9H-Fluoren-2-yl)-(2-fluoro-benzyl)-amine

[0350] 263 Dibenzofuran-4-yl-(2,5-dimethoxy-benzyl)-amine

[0351] 264 Dibenzofuran-4-yl-(2,3-dimethoxy-benzyl)-amine

[0352] 265 2-(Dibenzofuran4-ylaminomethyl)-phenol

[0353] 266 Dibenzofuran-4-yl-(2-methoxy-benzyl)-amine

[0354] 267 (2,5-Dimethoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)-amine

[0355] 268 (2,3-Dimethoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)-amine

[0356] 269 (2-Methoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)-amine

[0357] 270 Dibenzofuran-2-yl-(2,5-dimethoxy-benzyl)-amine

[0358] 271 Dibenzofuran-2-yl-(4-methoxy-benzyl)-amine

[0359] 272 (2-Bromo-benzyl)-dibenzofuran-2-yl-amine

[0360] 273 (8-Fluoro-dibenzofuran-2-yl)-(3H-imidazol-4-ylmethyl)-amine

[0361] 274 2-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]-benzonitrile

[0362] 275 (2-Ethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0363] 276 (8-Fluoro-dibenzofuran-2-yl)-(4-methylsulfanyl-benzyl)-amine

[0364] 277 (2-Bromo-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0365] 278 (8-Fluoro-dibenzofuran-2-yl)-quinolin-4-ylmethyl-amine

[0366] 279 (8-Fluoro-dibenzofuran-2-yl)-quinolin-2-ylmethyl-amine

[0367] 280 Dibenzofuran-2-yl-naphthalen-1-ylmethyl-amine

[0368] 281 (8-Fluoro-dibenzofuran-2-yl)-naphthalen-2-ylmethyl-amine

[0369] 282 (8-Fluoro-dibenzofuran-2-yl)-naphthalen-1-ylmethyl-amine

[0370] 283 Dibenzofuran-2-yl-(2-nitro-benzyl)-amine

[0371] 284 Dibenzofuran-2-yl-(3H-imidazol-4-ylmethyl)-amine

[0372] 285 2-(Dibenzofuran-2-ylaminomethyl)-benzonitrile

[0373] 286 Dibenzofuran-2-yl-(2-ethoxy-benzyl)-amine

[0374] 287 Dibenzofuran-2-yl-(3-trifluoromethyl-benzyl)-amine

[0375] 288 (4-tert-Butyl-benzyl)-dibenzofuran-2-yl-amine

[0376] 289 Dibenzofuran-2-yl-(3-fluoro-benzyl)-amine

[0377] 290 (2,5-Dimethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0378] 291 (2,3-Dimethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0379] 292 (4-Benzyloxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0380] 293 (3-Benzyloxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0381] 294 (4-Chloro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0382] 295 (3-Chloro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0383] 296 (2-Chloro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0384] 297 4-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]-phenol

[0385] 298 3-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]-phenol

[0386] 299 Dibenzofuran-2-yl-(2-fluoro-benzyl)-amine

[0387] 300 (8-Fluoro-dibenzofuran-2-yl)-(4-methoxy-benzyl)-amine

[0388] 301 (8-Fluoro-dibenzofuran-2-yl)-(3-methoxy-benzyl)-amine

[0389] 302 (8-Fluoro-dibenzofuran-2-yl)-(2-methoxy-benzyl)-amine

[0390] 303 (8-Fluoro-dibenzofuran-2-yl)-(4-trifluoromethyl-benzyl)-amine

[0391] 304 (8-Fluoro-dibenzofuran-2-yl)-(3-trifluoromethyl-benzyl)-amine

[0392] 305 (4-tert-Butyl-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0393] 306 (4-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0394] 307 (3-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0395] 308 (2-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0396] 309 (8-Fluoro-dibenzofuran-2-yl)-(4-methyl-benzyl)-amine

[0397] 310 (8-Fluoro-dibenzofuran-2-yl)-(3-methyl-benzyl)-amine

[0398] 311 Dibenzofuran-2-yl-(2,6-dimethoxy-benzyl)-amine

[0399] 312 Dibenzofuran-2-yl-(2,4-dimethoxy-benzyl)-amine

[0400] 313 Dibenzofuran-2-yl-(2,3-dimethoxy-benzyl)-amine

[0401] 314 (4Benzyloxy-benzyl)-dibenzofuran-2-yl-amine

[0402] 315 Dibenzofuran-2-yl-(3-methyl-benzyl)-amine

[0403] 316 (3-Chloro-benzyl)-dibenzofuran-2-yl-amine

[0404] 317 3-(Dibenzofuran-2-ylaminomethyl)-phenol

[0405] 318 (2-Chloro-benzyl)-dibenzofuran-2-yl-amine

[0406] 319 Dibenzofuran-2-yl-(3-methoxy-benzyl)-amine

[0407] 320 Dibenzofuran-2-yl-(2-methoxy-benzyl)-amine

[0408] 321 (9H-Fluoren-2-yl)-(2-methyl-benzyl)-amine

[0409] 322 Dibenzofuran-4-yl-(2-methyl-benzyl)-amine

[0410] 323 (8-Chloro-dibenzofuran-2-yl)-(2-methyl-benzyl)-amine

[0411] 324 (2-Methyl-benzyl)-(10H-phenothiazin-2-yl)-amine

[0412] 325 Dibenzo[b,e][1,4]dioxin-2-yl-(2-methyl-benzyl)-amine

[0413] 326 Dibenzofuran-2-yl-(2,6-difluoro-benzyl)-amine

[0414] 327 Dibenzofuran-2-yl-(2,5-difluoro-benzyl)-amine

[0415] 328 Dibenzofuran-2-yl-(2,4-difluoro-benzyl)-amine

[0416] 329 Dibenzofuran-2-yl-(2,3-difluoro-benzyl)-amine

[0417] 330 (8-Fluoro-dibenzofuran-2-yl)-thiophen-2-ylmethyl-amine

[0418] 331 Dibenzofuran-2-yl-(2,5-dimethyl-benzyl)-amine

[0419] 332 (8-Fluoro-dibenzofuran-2-yl)-thiophen-3-ylmethyl-amine

[0420] 333 (8-Fluoro-dibenzofuran-2-yl)-furan-2-ylmethyl-amine

[0421] 334 (8-Fluoro-dibenzofuran-2-yl)-furan-3-ylmethyl-amine

[0422] 335(8-Fluoro-dibenzofuran-2-yl)-(6-methyl-pyridin-2-ylmethyl)-amine

[0423] 336 (8-Fluoro-dibenzofuran-2-yl)-(4-methanesulfonyl-benzyl)-amine

[0424] 337 (8-Fluoro-dibenzofuran-2-yl)-pyridin-4-ylmethyl-amine

[0425] 338 (8-Fluoro-dibenzofuran-2-yl)-pyridin-3-ylmethyl-amine

[0426] 339 (8-Fluoro-dibenzofuran-2-yl)-pyridin-2-ylmethyl-amine

[0427] 340(8-Fluoro-dibenzofuran-2-yl)-(3-fluoro-4-methoxy-benzyl)-amine

[0428] 341 Dibenzofuran-2-yl-(2,4-dimethyl-benzyl)-amine

[0429] 342 (8-Fluoro-dibenzofuran-2-yl)-(3-fluoro-2-methyl-benzyl)-amine

[0430] 343 (8-Fluoro-dibenzofuran-2-yl)-(2,3,6-trifluoro-benzyl)-amine

[0431] 344 (8-Fluoro-dibenzofuran-2-yl)-(2,3,4-trifluoro-benzyl)-amine

[0432] 345 (3,5-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0433] 346 (3,4-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0434] 347 (3,5-difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0435] 348 (2,6-Difluoro-benzyl(2,5-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0436] 349 (2,4-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0437] 350 (2,3-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0438] 351 (2,5-Dimethyl-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0439] 352 (2,4-Dimethyl-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0440] 353(2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0441] 354 (3,5-Dimethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine

[0442] 355 Dibenzofuran-2-yl-dibenzofuran-2-ylmethyl-amine

[0443] 356 Dibenzofuran-2-yl-dibenzofuran-3-ylmethyl-amine

[0444] 357 Dibenzofuran-2-yl-(6-methyl-pyridin-2-ylmethyl)-amine

[0445] 358 Dibenzofuran-2-yl-(4-methanesulfonyl-benzyl)-amine

[0446] 359 Dibenzofuran-2-yl-pyridin-4-ylmethyl-amine

[0447] 360 Dibenzofuran-2-yl-pyridin-3-ylmethyl-amine

[0448] 361 Dibenzofuran-2-yl-pyridin-2-ylmethyl-amine

[0449] 362 Dibenzofuran-2-yl-(3-fluoro-4-methoxy-benzyl)-amine

[0450] 363 Dibenzofuran-2-yl-(3-fluoro-2-methyl-benzyl)-amine

[0451] 364 Dibenzofuran-2-yl-(2,3,6-trifluoro-benzyl)-amine

[0452] 365 Dibenzofuran-2-yl-(2,3,4-trifluoro-benzyl)-amine

[0453] 366 Dibenzofuran-2-yl-(3,5-difluoro-benzyl)-amine

[0454] 367 Dibenzofuran-2-yl-(3,4-difluoro-benzyl)-amine

[0455] 368 Dibenzofuran-2-yl-(3,4-dimethoxy-benzyl)-amine

[0456] 369 Dibenzofuran-2-yl-methyl-(2-methyl-benzyl)-amine

[0457] 370 Dibenzothiohen-2-yl-(2,4-dimethyl-benzyl)-amine

[0458] 371 (4-tert-Butyl-benzyl)-dibenzothiohen-2-yl-amine

[0459] 372 (2-Chloro-benzyl)-dibenzothiohen-2-yl-amine

[0460] 373 Dibenzothiohen-2-yl-(2,6-difluoro-benzyl)-amine

[0461] 374 Dibenzothiohen-2-yl-(2,3,6-trifluoro-benzyl)-amine

[0462] 375 Dibenzothiohen-2-yl-(2-fluoro-benzyl)-amine

[0463] 376 Benzyl-dibenzothiohen-2-yl-amine

[0464] 377 Dibenzothiohen-2-yl-(4-methoxy-benzyl)-amine

[0465] 378 Dibenzothiohen-2-yl-(2,3-dimethoxy-benzyl)-amine

[0466] 379 Dibenzothiohen-2-yl-(2,5-difluoro-benzyl)-amine

[0467] 380 Dibenzothiohen-2-yl-(3-methoxy-benzyl)-amine

[0468] 381 Dibenzothiohen-2-yl-(2,3,4-trifuoro-benzyl)-amine

[0469] 382 (-2-Bromo-benzyl)-dibenzothiohen-2-yl-amine

[0470] 383Dibenzothiohen-2-yl-(2,3-dihydro-1,4benzodioxin-6-ylmethyl)-amine

[0471] 384 Dibenzothiohen-2-yl-(3-fluoro-4-methoxy-benzyl)-amine

[0472] 385 Dibenzothiohen-2-yl-(2,5-dimethyl-benzyl)-amine

[0473] 386 Dibenzothiohen-2-yl-thiophen-3-ylmethyl-amine

[0474] 387 Dibenzothiohen-2-yl-naphthalene-1-ylmethyl-amine

[0475] 388 Dibenzothiohen-2-yl-(2-trifluoromethyl-benzyl)-amine

[0476] 389 Dibenzothiohen-2-yl-naphthalen-2-ylmethyl-amine

[0477] 390 Dibenzothiohen-2-yl-(2-ethoxy-benzyl)-amine

[0478] 391(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3-fluoro-2-methyl-benzyl)-amine

[0479] 392(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2-methyl-benzyl)-amine

[0480] 393(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,4-dimethyl-benzyl)-amine

[0481] 394(4-tert-Butyl-benzyl)-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine

[0482] 395(2-Chloro-benzyl)-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine

[0483] 396(2,6-Difluoro-benzyl)-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine

[0484] 397(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,3,6-trifluoro-benzyl)-amine

[0485] 398(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2-fluoro-benzyl)-amine

[0486] 399(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3,5-dimethoxy-benzyl)-amine

[0487] 400 Benzyl-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine

[0488] 401(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(4-methoxy-benzyl)-amine

[0489] 402(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,3-dimethoxy-benzyl)-amine

[0490] 403(2,5-difluoro-benzyl)-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine

[0491] 404 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3-methoxy-benzyl)-amine

[0492] 405(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,3,-trifluoro-benzyl)-amine

[0493] 406(2-Bromo-benzyl)-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine

[0494] 407(2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine

[0495] 408(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3-fluoro-4-methoxy-benzyl)-amine

[0496] 409(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,5-dimethyl-benzyl)-amine

[0497] 410(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-thiophen-3-ylmethyl-amine

[0498] 411(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-naphthalen-1-ylmethyl-amine

[0499] 412(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2-trifluoromethyl-benzyl)-amine

[0500] 413(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-naphthalen-2-ylmethyl-amine

[0501] 414(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2-ethoxy-benzyl)-amine

[0502] 415 (3-Fluoro-2-methyl-benzyl)-(10H-phenothiazin-2-yl)-amine

[0503] 416 (2,4-Dimethyl-benzyl)-(10H-phenothiazin-2-yl)-amine

[0504] 417 (4-tert-Butyl-benzyl)-(10H-phenothiazin-2-yl)-amine

[0505] 418 (2-Chloro-benzyl)-(10H-phenothiazin-2-yl)-amine

[0506] 419 (2,6-Difluoro-benzyl)-(10H-phenothiazin-2-yl)-amine

[0507] 420 (10H-Phenothiazin-2-yl)-(2,3,6-trifluorobenzyl)-amine

[0508] 421 (2-Fluoro-benzyl)-(10H-phenothiazin-2-yl)-amine

[0509] 422 (3,5-Dimethoxy-benzyl)-(10H-phenothiazin-2-yl)-amine

[0510] 423 Benzyl-(10H-phenothiazin-2-yl)-amine

[0511] 424 (4-Methoxy-benzyl)-(10H-phenothiazin-2-yl)-amine

[0512] 425 (2,5-Difluoro-benzyl)-(10H-phenothiazin-2-yl)-amine

[0513] 426 (10H-Phenothiazin-2-yl)-(2,3,4-trifluoro-benzyl)-amine

[0514] 427(2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-(10H-phenothiazin-2-yl)-amine

[0515] 428 (3-Fluoro-4-methoxy-benzyl)-(10H-phenothiazin-2-yl)-amine

[0516] 429 (2,5-Dimethyl-benzyl)-(10H-phenothiazin-2-yl)-amine

[0517] 430 (10H-Phenothiazin-2-yl)-thiophen-3-ylmethyl-amine

[0518] 431 (10H-Phenothiazin-2-yl)-(2-trifluoromethyl-benzyl)-amine

[0519] 432 (9H-Carbazol-3-yl)-(3-fluoro-2-methyl-benzyl)-amine

[0520] 433 (9H-Carbazol-3-yl)-(2-methyl-benzyl)-amine

[0521] 434 (9H-Carbazol-3-yl)-(2,4-dimethyl-benzyl)-amine

[0522] 435 (4-tert-Butyl-benzyl)-(9H-carbazol-3-yl)-amine

[0523] 436 (9H-Carbazol-3-yl)-(2-chloro-benzyl)-amine

[0524] 437 (9H-Carbazol-3-yl)-(2,6-difluoro-benzyl)-amine

[0525] 438 (9H-Carbazol-3-yl)-(2,3,6-trifluoro-benzyl)-amine

[0526] 439 (9H-Carbazol-3-yl)-(3,5-dimethoxy-benzyl)-amine

[0527] 440 (9H-Carbazol-3-yl)-(2,3-dimethoxy-benzyl)-amine

[0528] 441 (9H-Carbazol-3-yl)-(2,5-difluoro-benzyl)-amine

[0529] 442 (9H-Carbazol-3-yl)-(2,3,4-trifluoro-benzyl)-amine

[0530] 443(9H-Carbazol-3-yl)-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-amine

[0531] 444 (9H-Carbazol-3-yl)-(2,5-dimethyl-benzyl)-amine

[0532] 445 (9H-Carbazol-3-yl)-naphthalen-1-ylmethyl-amine

[0533] 446 (9H-Carbazol-3-yl)-naphthalen-2-ylmethyl-amine

[0534] 447Dibenzofuran-2-yl-bis-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-amine

[0535] 448 Dibenzofuran-2-yl-bis-thiophen-3-ylmethyl-amine

[0536] 449 Dibenzofuran-2-yl-(4-phenoxy-benzyl)-amine

[0537] 450 2-Dibenzofuran-2-yl-2,3-dihydro-1H-isoindole

[0538] 451 2-Dibenzofuran-2-yl-1H-isoindole-1,3-dione

[0539] 452 Dibenzofuran-2-yl-(4-trifluoromethoxy-benzyl)-amine

[0540] 453 Dibenzofuran-2-yl-(2-methoxy-benzyl)-amine

[0541] 454 Dibenzofuran-2-yl-(3-phenoxy-benzyl)-amine

[0542] 455 Dibenzofuran-2-yl-methyl(2-methyl-benzyl)-amine

[0543] 456 Dibenzofuran-2-yl-(1-phenyl-butyl)-amine

[0544] 457 Dibenzofuran-2-yl-phenethyl-amine

[0545] 458 Dibenzofuran-2-yl-(1-phenyl-ethyl)-amine

EXAMPLES

[0546] General M + H MOLECULAR Example MOLSTRUCTURE procedure (APCl)*FORMULA 1

7 282 C18 H19 N O2 2

7 250 C18 H19 H 3

7 250 C18 H19 N 4

7 293 C20 H24 N2 5

5 256 C16 H17 N O2 6

5 314 C18 H19 N O2S 7

5 310 C20 H23 N O2 8

5 284 C18 H21 N O2 9

5 270 C17 H19 N O2 10

7, 5 308 C20 H25 N3 11

5 371 C26 H30 N2 12

5, 7 265 C18 H20 N2 13

5 328 C24 H25 N 14

5, 7 238 C17 H19 N 15

5 346 C18 H19 N O4S 16

6 322 C22 H27 N O 17

6 320 C22 H25 N O 18

6 318 C22 H23 N O 19

6 348 C24 H29 N O 20

6 278 C19 H19 N O 21

6 322 C22 H27 N O 22

6 292 C20 H21 N O 23

6 252 C17 H17 N O 24

6, 5 296 C19 H21 N O2 25

6, 5 264 C19 H21 N 26

4 360 C20 H25 N O S2 27

4 324 C22 H29 N O 28

4 268 C18 H21 N O 29

5 357 C20 H24 N2 O2 S 30

5, 7 267 C18 H22 N2 31

5, 7 325 C20 H24 N2 S 32

5, 7 307 C21 H26 N2 33

5, 7 321 C22 H28 N2 34

5 295 C20 H26 N2 35

5 293 C20 H24 N2 36

5, 7 281 C19 H24 N2 37

5, 7 224 C16 H17 N 38

5 282 C18 H19 N S 39

5, 7 278 C20 H23 N 40

5 316 C17 H17 N O3 S 41

5, 6 267 C17 H18 N2 O 42

5, 6 226 C15 H15 N O 43

5, 6 266 C18 H19 N O 44

5 252 C17 H17 N O 45

5 316 C17 H17 N O3 S 46

5 267 C17 H18 N2 O 47

5 226 C15 H15 N O 48

5 284 C17 H17 N O S 49

5 266 C18 H19 N O 50

5 280 C19 H21 N O 51

5 308, 310 C19 H14 Cl N O 52

2 353. 355 C19 H13 Cl N2 O3 53

2 358 C20 H14 F3 N O2 54

2 318 C20 H15 N O3 55

2 332 C21 H17 N O3 56

2 334 C21 H19 N O3 57

2 342 C20 H14 F3 N O 58

1, 2, 3 288 C20 H17 N O 59

2 280 C17 H13 N O S 60

2 319 C19 H14 N2 O3 61

2 320 C20 H17 N O S 62

2 288 C20 H17 N O 63

2 274 C19 H15 N O 64

2 380 C26 H21 N O2 65

5 330 C23 H23 N O 66

5 332 C22 H21 N O2 67

5 270 C17 H19 N O2 68

5 268 C18 H21 N O 69

5 254 C17 H19 N O 70

5 268 C18 H21 N O 71

5 294 C20 H23 N O 72

5 294 C20 H23 N O 73

5, 6 280 C19 H21 N O 74

5, 6 284 C17 H17 N O S 75

5 270 C16 H15 N O S 76

5 254 C17 H19 N O 77

5 254 C17 H19 N O 78

5, 6 240 C16 H17 N O 79

3 293 C18 H13 F N2 O 80

3 276 C17 H13 N3 O 81

3 289 C19 H16 N2 O 82

3 321 C20 H17 F N2 O 83

3 354 C23 H19 N3 O 85

3 381 C21 H20 N2 O3 S 86

3 304 C19 H17 N3 O 87

3 317 C21 H20 N2 O 88

3, 2 355 C23 H18 N2 S 89

3 383 C20 H18 N2 O2 S 90

3 339 C19 H15 F N2 O S 91

3 325 C18 H13 F N2 O S 92

3 358 C21 H15 N3 O S 93

3 357 C22 H16 N2 O S 94

3 385 C19 H16 N2 O3 S 95

3 308 C17 H13 N3 O S 96

3 321 C19 H16 N2 O S 97

3 335 C24 H18 N2 98

3 362 C22 H19 N O2 S 99

3 285 C20 H16 N2 100

3 298 C22 H19 N 101

3 322 C20 H16 F N O2 102

3 308 C19 H14 F N O2 103

3 341 C22 H16 N2 O2 104

3 340 C23 H17 N O2 105

3 368 C20 H17 N O4 S 106

3 291 C18 H14 N2 O2 107

3 322 C20 H16 F N O2 108

3 308 C19 H14 F N O2 109

3 368 C20 H17 N O4 S 110

3 291 C18 H14 N2 O2 111

3 304 C20 H17 N O2 112

3 326, 328 C19 H13 Cl F N O 113

3 359 C23 H16 Cl N O 114

3 387 C20 H16 Cl N O3 S 115

3 355 C20 H22 N2 O2 S 116

3 278 C18 H19 N3 117

3 307 C19 H15 F N2 O 118

2, 3 325 C22 H16 N2 O 119

2 325 C22 H16 N2 O 120

2 335 C21 H19 F N2 O 121

2 317 C21 H20 N2 O 122

2 325 C17 H12 N2 O3 S 123

2 281 C16 H12 N2 O S 124

2 292 C19 H14 F N O 125

2 333 C21 H20N2O2 126

2 363 C22H22N2O3 127

2 359 C24H26N2O1 128

2 303 C20H18N2O1 129

2 328 C21H17N3O1 130

2 336 C20H17N1O2S1 131

2 338, 340 C20H16N1O2Cl1 132

2 336 C20H17O2S1N1 133

2 366 C21H19O3N1S1 134

2 354 C20H16O2N1S1F1 135

2 362 C23H23O1N1S1 136

2 306 C19H15N1O1S1 137

2 350 C21H19N1O2S1 138

2 368, 370 C21H18N1O3Cl1 139

2 356, 358 C20H15N1O2Cl1F1 140

2 308, 310 C19H14NOCl 141

2 302 C21H19NO 142

2 315, 317 C15H11N2OClS 143

2 302 C21H19NO 144

2 332 C22H21NO2 145

2 320 C21H18NOF 146

2 328 C24H25N 147

2 272 C20H17N1 148

2 279 C16H14N2S 149

2 316 C22H21NO 150

2 304 C20H17NO2 151

2 334 C20H13N2Ocl 152

2 304 C20H17NO2 153

2 334 C21H19NO3 154

2 322 C20H16NFO2 155

2 330 C23H23NO 156

2 318 C21H19NO2 157

2 333 C21H20N2O2 158

2 338, 340 C20H16NO2Cl 159

2 352, 354 C21H18NO2Cl 160

2 302 C21 H19 N O 161

2 309 C18 H16 N2 O S 162

2 304 C19 H17 N3 O 163

2 383, 385 C19 H14 Br N O S 164

2 357 C22 H16 N2 O S 165

2 312 C17 H13 N O S2 166

2 321 C19 H16 N2 O S 167

2 307 C18 H14 N2 O S 168

2 307 C18 H14 N2 O S 169

2 314, 316 C17 H12 Cl N O S 170

2 379, 381 C21 H19 Br N2 171

2 323, 325 C19 H15 Cl N2 O 172

2 307 C19 H18 N2 S 173

2 341, 342 C19 H17 Cl N2 S 174

2 3O2 C20 H19 N3 175

2 350, 352 C20 H16 Br N 176

2, 3 309, 311 C18 H13 Cl N2 O 177

2 323 C23 H18 N2 178

2 278 C18 H15 N S 179

2 287 C20 H18 N2 180

2 273 C19 H16 N2 181

2 273 C19 H16 N2 182

2 273 C19 H16 N2 183

2 309, 311 C18 H13 Cl N2 O 184

2 325 C22 H16 N2 O 185

2 325 C22 H16 N2 O 186

2 280 C17 H13 N O S 187

2 289 C19 H16 N2 O 188

2 275 C18 H14 N2 O 189

2 275 C18 H14 N2 O 190

2 275 C18 H14 N2 O 191

2 387, 389 C19 H13 Br Cl N O 192

2 309, 311 C18 H13 Cl N2 O 193

2 357 C20 H15 F3 N2 O 194

2 357 C20 H15 F3 N2 O 195

2 339 C20 H16 F2 N2 O 196

2 339 C20 H16 F2 N2 O 197

2 339 C20 H16 F2 N2 O 198

2 339 C20 H16 F2 N2 O 199

2 331 C22 H22 N2 O 200

2 331 C22 H22 N2 O 201

2 361 C22 H20 N2 O3 202

2 338 C20 H16 F N O S 203

2 363 C19 H11 Cl F3 N O 204

2 360 C19 H12 F3 N O S 205

2 360 C19 H12 F3 N O S 206

2 342 C19 H13 F2 N O S 207

2 342 C19 H13 F2 N O S 208

2 342 C19 H13 F2 N O S 209

2 342 C19 H13 F2 N O S 210

2 334 C21 H19 N O S 211

2 364 C21 H17 N O3 S 212

2 272 C16 H14 F N S 213

2 363 C19 H11 Cl F3 N O 214

2 345 C19 H12 Cl F2 N O 215

2 345 C19 H12 Cl F2 N O 216

2 345 C19 H12 Cl F2 N O 217

2 333 C22 H21 F N2 218

2 345 C19 H12 Cl F2 N O 219

2 355 C21 H17 F3 N2 220

2 355 C21 H17 F3 N2 221

2 337 C21 H18 F2 N2 222

2 337 C21 H18 F2 N2 223

2 337 C21 H18 F2 N2 224

2 337 C21 H18 F2 N2 225

2 329 C23 H24 N2 226

2 329 C23 H24 N2 227

2 359 C23 H22 N2 O2 228

2 304 C21 H18 F N 229

2 337 C21 H18 Cl N O 230

2 326 C20 H14 F3 N 231

2 326 C20 H14 F3 N 232

2 308 C20 H15 F2 N 233

2 308 C20 H15 F2 N 234

2 308 C20 H15 F2 N 235

2 300 C22 H21 N 236

2 300 C22 H21 N 237

2 330 C22 H19 N O2 238

2 336, 338 C21 H18 Cl N O 239

2 302 C21 H19 N O 240

2 306 C20 H16 F N O 241

2, 3 335 C21 H19 F N2 O 242

2, 3 341 C20 H15 Cl F N O 243

2 367 C21 H16 Cl N O3 244

2 366 C21 H19 N O3 S 245

2 366 C21 H19 N O3 S 246

2 340, 342 C19 H14 Cl N O S 247

2 336 C20 H17 N O2 S 248

2 320 C20 H17 N O S 249

2 318, 320 C21 H16 Cl N 250

2 302 C21 H16 F N 251

2 350 C21 H19 N O4 252

2 324, 326 C19 H14 Cl N O2 253

2 306 C19 H15 N O3 254

2 320 C20 H17 N O3 255

2 317 C21 H20 N2 O 256

2 319 C21 H19 F N2 257

2 315 C22 H22 N2 258

2 306, 308 C20 H16 Cl N 259

2 288 C20 H17 N O 260

2 3O2 C21 H19 N O 261

2 340 C21 H16 F3 N 262

2 290 C20 H16 F N 263

2 334 C21 H19 N O3 264

2 334 C21 H19 N O3 265

2 290 C19 H15 N O2 266

2 304 C20 H17 N O2 267

2 364 C22 H21 N O4 268

2 364 C22 H21 N O4 269

2 334 C21 H19 N O3 270

2 334 C21 H19 N O3 271

2 304 C20 H17 N O2 272

2 351, 353 C19 H14 Br N O 273

2 282 C16 H12 F N3 O 274

2 317 C20 H13 F N2 O 275

2 336 C21 H18 F N O2 276

2 338 C20 H16 F N O S 277

2 369, 371 C19 H13 Br F N O 278

2 343 C22 H15 F N2 O 279

2 343 C22 H15 F N2 O 280

2, 3 324 C23 H17 N O 281

2 342 C23 H16 F N O 282

2 342 C23 H16 F N O 283

2 319 C19 H14 N2 O3 284

2 264 C16 H13 N3 O 285

2 299 C20 H14 N2 O 286

2 318 C21 H19 N O2 287

2 342 C20 H14 F3 N O 288

2 330 C23 H23 N O 289

2 292 C19 H14 F N O 290

2 352 C21 H18 F N O3 291

2 352 C21 H18 F N O3 292

2 398 C26 H20 F N O2 293

2 398 C26 H20 F N O2 294

2 326, 328 C19 H13 Cl F N O 295

2 326, 328 C19 H13 Cl F N O 296

2 326, 328 C19 H13 Cl F N O 297

2 308 C19 H14 F N O2 298

2, 3 308 C19 H14 F N O2 299

2 292 C19 H14 F N O 300

2 322 C20 H16 F N O2 301

2 322 C20 H16 F N O2 302

2 322 C20 H16 F N O2 303

2 360 C20 H13 F4 N O 304

2 360 C20 H13 F4 N O 305

2 348 C23 H22 F N O 306

2 310 C19 H13 F2 N O 307

2 310 C19 H13 F2 N O 308

2, 3 310 C19 H13 F2 N O 309

2 306 C20 H16 F N O 310

2 306 C20 H16 F N O 311

2 334 C21 H19 N O3 312

2 334 C21 H19 N O3 313

2 334 C21 H19 N O3 314

2 380 C26 H21 N O2 315

2 288 C20 H17 N O 316

2 308, 310 C19 H14 Cl N O 317

2 290 C19 H15 N O2 318

2 308, 310 C19 H14 Cl N O 319

2 304 C20 H17 N O2 320

2 304 C20 H17 N O2 321

2 286 C21 H19 N 322

2 288 C20 H17 N O 323

2, 3 323 C20 H16 Cl N O 324

2 319 C20 H18 N2 S 325

2, 3 304 C20 H17 N O2 326

2 310 C19 H13 F2 N O 327

2 310 C19 H13 F2 N O 328

2 310 C19 H13 F2 N O 329

2 310 C19 H13 F2 N O 330

2 298 C17 H12 F N O S 331

2 302 C21 H19 N O 332

2 298 C17 H12 F N O S 333

2 282 C17 H12 F N O2 334

2 282 C17 H12 F N O2 335

2 307 C19 H15 F N2 O 336

2 370 C20 H16 F N O3 S 337

2, 3 293 C18 H13 F N2 O 338

2 293 C18 H13 F N2 O 339

2 293 C18 H13 F N2 O 340

2 340 C20 H15 F2 N O2 341

2 302 C21 H19 N O 342

2, 3 324 C20 H15 F2 N O 343

2 346 C19 H11 F4 N O 344

2 346 C19 H11 F4 N O 345

2 328 C19 H12 F3 N O 346

2 328 C19 H12 F3 N O 347

2 328 C19 H12 F3 N O 348

2 328 C19 H12 F3 N O 349

2 328 C19 H12 F3 N O 350

2 328 C19 H12 F3 N O 351

2 320 C21 H18 F N O 352

2 320 C21 H18 F N O 353

2 350 C21 H16 F N O3 354

2 352 C21 H18 F N O3 355

2 264 C17 H13 N O2 356

2 264 C17 H13 N O2 357

2 289 C19 H16 N2 O 358

2, 3 352 C20 H17 N O3 S 359

2, 3 275 C18 H14 N2 O 360

2 275 C18 H14 N2 O 361

2 275 C18 H14 N2 O 362

2 322 C20 H16 F N O2 363

2, 3 306 C20 H16 F N O 364

2 328 C19 H12 F3 N O 365

2 328 C19 H12 F3 N O 366

2 310 C19 H13 F2 N O 367

2 310 C19 H13 F2 N O 368

2 334 C21 H19 N O3 369

2 304 C20H17NS 370

2 318 C21H19NS 371

2 346 C23H23NS 372

2 323, 325 C19H14ClNS 373

2 326 C19H13F2NS 374

2 344 C19H12F3NS 375

2 308 C19H14FNS 376

2 290 C19H15NS 377

2 320 C20H17NOS 378

2 350 C21H19NO2S 379

2 326 C19H13F2NS 380

2 320 C20H17NOS 381

2 344 C19H12F3NS 382

2 369 C19H14BrNS 383

2 348 C21H17NO2S 384

2 338 C20H16FNOS 385

2 318 C21H19NS 386

2 296 C17H13NS2 387

2 340 C23H17NS 388

2 358 C20H14F3NS 389

2 340 C23H17NS 390

2 334 C21H19NOS 391

2 333 C22H21FN2 392

2 315 C22H22N2 393

2 329 C23H24N2 394

2 357 C25H28N2 395

2 334, 336 C21H19ClN2 396

2 337 C21H18F2N2 397

2 355 C21H17F3N2 398

2 319 C21H19FN2 399

2 361 C23H24N2O2 400

2 301 C21H20N2 401

2 331 C22H22N2O 402

2 361 C23H24N2O2 403

2 337 C21H18F2N2 404

2 331 C22H22N2O 405

2 355 C21H17F3N2 406

2 380 C21H19BrN2 407

2 359 C23H22N2O2 408

2 349 C22H21FN2O 409

2 329 C23H24N2 410

2 307 C19H18N2S 411

2 351 C25H22N2 412

2 369 C22H19F3N2 413

2 351 C25H22N2 414

2 345 C23H24N2O 415

2 337 C20H17FN2S 416

2 333 C21H20N2S 417

2 361 C23H24N2S 418

2 338, 340 C19H15ClN2S 419

2 341 C19H14F2N2S 420

2 359 C19H13F3N2S 421

2 323 C19H15FN2S 422

2 365 C21H20N2O2S 423

2 305 C19H16N2S 424

2 335 C20H18N2OS 425

2 341 C19H14F2N2S 426

2 359 C19H13F3N2S 427

2 363 C21H18N2O2S 428

2 353 C20H17FN2OS 429

2 333 C21H2ON2S 430

2 311 C17H14N2S2 431

2 373 C20H15F3N2S 432

2 305 C20H17FN2 433

2 287 C20H18N2 434

2 301 C21H20N2 435

2 329 C23H24N2 436

2 306, 308 C19H15ClN2 437

2 309 C19H14F2N2 438

2 327 C19H13F3N2 439

2 333 C21H20N2O2 440

2 333 C21H20N2O2 441

2 309 C19H14F2N2 442

2 327 C19H13F3N2 443

2 331 C21H18N2O2 444

2 301 C21H20N2 445

2 323 C23H18N2 446

2 323 C23H18N2

[0547] The following compound were prepared to the general procedure 1:MS (M + H) ¹H-NMR in CDCl₃ unless Mp Example Structure APCI otherwisenoted (δ) (° C.)  26

360 7.90(1H, d); 7.51(1H, d); 7.44-7.26(4H, m); 6.95(1H, d); 3.46(4H,t); 2.58(4H, t); 2.12(6H, s); 1.91(4H, quintet) —  55

332 7.87(1H, d); 7.52(1H, d); 7.38-7.46(2H, quartet); 7.25-7.35(1H, t);7.14(1H, s); 6.97-6.86(3H, m); 6.76-6.81(1H, d); 4.31 (2H, s) 4.25(4H,br s) — 447

480 7.81(1H, d); 7.48(1H, d); 7.34-7.41(2H, m); 7.22-7.28(2H, t);6.88-6.92(1H, d); 6.74-6.86(6H, m); 4.56(4H, br s); 4.23(8H, br s) — 448

376 7.85(1H, d); 7.51(1H, d); 7.26-7.42(6H, m); 7.08(2H, br s);6.99-7.06(3H, m); 4.60(4H, br s) 109-110  59

280 7.86(1H, d); 7.52(1H, d); 7.38-7.44(2H, m); 7.25-7.35(3H, m);7.19(1H, s); 7.14(1H, s); 6.81(1H, s); 4.43(2H, s) 62-63  56

334 7.86(1H, d); 7.52(1H, d); 7.29-7.42(3H, m); 7.12(1H, s); 6.78(1H,d); 6.60(2H, s); 6.41(1H, t); 4.35(2H, s); 3.79(6H, s) 87-88  63

274 7.89(1H, d); 7.53(1H, d); 7.31-7.48(8H, m); 7.18(1H, s); 6.81(1H,d); 4.43(2H, s); 4.10(1H, br s) 81-82  61

320 IN DMSO 7.93(1H, d); 7.54(1H, d); 7.17-7.42(8H, m); 6.81(1H, d);6.22(1H, t); 4.30(2H, d); 2.41(3H, s) 103-104  73

294 7.90(1H, d); 7.51(1H, d); 7.36-7.44(2H, quartet); 7.26-7.33(1H, t);7.09(1H, s); 6.72(1H, d); 3.60(2H, br m); 1.95(2H, br m); 1.61 (12H, brm) 50-52  57

342 7.86(1H, d); 7.63(2H, d); 7.54(3H, t); 7.43(2H, quartet); 7.32(1Ht); 7.11(1H, s); 6.77(1H, d); 4.46(2H, s) 4.15(1H, br s) 89-90 449

364 7.90(1H, d); 7.53(1H, d); 7.30-7.45(7H, m); 7.03-7.18(6H, m);6.81(1H, d); 4.39(2H, s); 4.08(1H, br s) 91-93 450

286 7.96(1H, d); 7.31-7.55(8H, m); 7.15(1H, s); 6.83(1H, d); 4.73(4H, s)193-195 451

314 IN DMSO 8.22(1H, s); 8.13(1H, d); 7.84-8.01(5H, m); 7.75(1H, d);7.57(2H, m); 7.43(1H, t) 217-218  58

288 7.95(1H, d); 7.57(1H, d); 7.28-7.41(4H, m); 7.12-7.20(4H, m);6.87(1H, d); 6.03(1H, t); 4.28(2H, d); 2.36(3H, s) 84-85 452

358 7.85(1H, d); 7.37-7.53(5H, m); 7.20-7.31(3H, m); 7.14(1H, s);6.90(1H, d); 4.43(2H, s); 4.22(1H, br s) 75-77 453

290 7.86(1H, d); 7.55(1H, d); 7.41-7.47(3H, t); 7.18-7.34(4H, m);6.89-7.02(3H, m); 4.52(2H, s) 145-147 454

366 7.85(1H, d); 7.51(1H, d); 7.26-7.44(6H, m); 7.17(1H, d);7.06-7.13(3H, m); 6.99-7.02(2H, m); 6.95(1H, s); 6.77(1H, dd) 4.40(2H,s); 4.17(1H, s) 93-94  54

316 7.86(1H, d); 7.51(1H, d); 7.26-7.43(3H, m); 7.14(1H, s);6.87-6.92(2H, m); 6.77-6.81(2H, m); 5.96(2H, s); 4.32(2H, s); 4.12(1H,br s) 85-86 455

302 7.99(1H, d); 7.52(1H, d); 7.44-7.39(2H, m); 7.32-7.15(6H, m);6.89(1H, s); 4.52(2H, s); 3.09(3H, s); 2.37(3H, s) 456

316 7.77(1H, d); 7.48-7.21(9H, m); 7.00(1H, d); 6.70(1H, dd); 4.40(1H,t); 4.13(1H, br s) 1.88-1.78(2H, m); 1.51-1.38(2H, m); 0.97(3H, t) — 457

392 7.87(1H, d); 7.53-7.26(9H, m); 7.16(1H, d); 6.77(1H, dd); 3.50(2H,t); 3.00(2H, t) — 458

288 7.76(1H, d); 7.48-7.21(9H, m); 6.99(1H, d); 6.70(1H, dd); 4.57(1H,q); 4.07(1H, br s); 1.57(3H, d) 94-95 202

338 7.09(4H, m), 7.09(3H, m), 6.96(1H, d), 6.30(2H, m), 4.26(sH, s),2.26(3H, s) — 210

334 7.26(1H, s), 7.18(1H, d), 7.09(s, 1H), 7.07(1H, s), 7.02(1H, s),6.95(1H, s), 6.97(2H, s), 6.96(1H, s), 6.87(1H, d), 6.36(1H, s),6.34(1H, d), 4.2(2H, s), 2.31 (6H, s). — 135

362 7.26(1H, s), 7.18(1H, d), 7.09(s, 1H), 7.07(1H, s), 7.02(1H, s),6.95(1H, s), 6.97(2H, s), 6.96(1H, s), 6.87(1H, d), 6.36(1H, s),6.34(1H, d), 4.2(2H, s), 1.3(9H, s). — 146

328 7.61(d, 1H), 7.58(d, 1H), 7.45(d, 1H), 7.39(d, 1H), 7.37(s, 1H),7.34(s, 1H), 7.32(s, 1H), 7.28(d, 1H), 7.16(t, 1H), 6.86(s, 1H),6.68(dd, 1H), 4.35(s, 3H), 3.8(s, 2H), 1.31(s, 9H). —  90

339 8.15(d, 1H), 7.22(s, 1H), 7.05(m, 3H), 6.98(m, 2H), 6.88(d, 1H),6.32(d, 1H), 6.29(s, 1H), 4.3(s, 2H), 2.3(s, 3H). —

[0548] Antiviral Activity Assays:

[0549] Screening assays: Anti-herpes simplex virus-1 (HSV) activity isdetermined in a yield reduction assay utilizing a recombinant HSV (HSVUS3: pgC-lacZ which expresses E. coli β-galactosidase (β-gal) under thecontrol of an HSV late gene promoter (Fink, D. J.; Sternberg, L. R.;Weber, P. C.; Mata, M.; Goins, W. F.; Glorioso, J. C. Human Gene Therapy3:11-19, 1992). Vero (African Green Monkey kidney) cells are infected ata multiplicity of infection of 0.01 with the virus, and serial dilutionsof the compound in dimethyl sulfoxide (DMSO) are added. The finalconcentration of DMSO in all wells is 1%. DMSO is added to controlwells. The infection is allowed to proceed for 2 days at which time theβ-gal activity in cell lysates is measured. Activity in wells containingcompound is compared to control wells and percent inhibition determined.The EC₅₀ is defined as the concentration of drug that produces a 50%reduction in β-gal production relative to control wells.

[0550] Anti-human cytomegalovirus (HCMV) activity is determined in ayield reduction assay utilizing a recombinant HCMV (RC256) that producesβ-gal (Spaete, R. R.; Mocarski, E. S. Proceedings of the NationalAcademy of Sciences USA 84:7213-7217, 1987). Primary human diploidfibroblasts (HFF cells) are infected at an moi of 0.01 with RC256, andserial dilutions of the compound in DMSO are added. The finalconcentration of DMSO in all wells is 1%. The infection is allowed toproceed for 7 days at which time the β-gal activity in cell lysates ismeasured. Activity in wells containing compound is compared to controlwells and percent inhibition determined. The EC₅₀ is defined as theconcentration of compound that produces a 50% reduction in β-galproduction relative to control wells. TC₅₀ is defined as concentrationof compound that produces cytotoxicity in 50% of uninfected cells.

[0551] Secondary yield reduction assays: To determine the activity ofcompounds against HSV, Vero cells are plated in 6 well dishes at adensity of 5×10⁵ cells/well. Cells are infected at a multiplicity ofinfection of 0.01 with HSV (strain Syn17+). 30 μL of one of sixthreefold serial dilutions of test compound in DMSO is added to eachwell at the time of infection. The plates are returned to a 37° C.incubator and the infection allowed to proceed for 2 days. Aliquots ofthe supernatant are harvested, and the virus titer determined. Verocells in 24 well plates are infected with threefold serial dilutions ofsupernatant. The virus is allowed to adsorb to the monolayer for 1.5hours, after which it is aspirated and replaced with growth mediumcontaining 0.5% methylcellulose. Plaques are allowed to develop for 5days, at which time the medium aspirated and the monolayer stained withcrystal violet. The plaques are enumerated under low powermagnification. Percent inhibition is determined by comparison with thetiter from cells infected in the presence of DMSO alone.

[0552] To determine the activity of compounds against CMV, HFF cells,plated in 24 well plates at 1×10⁵ cells/well, are infected with CMV(strain AD169) at an moi of 0.01. 10 μL of one of six threefolddilutions of test compound in DMSO is added to each well at the time ofinfection. The plates are returned to a 37° C. incubator and theinfection allowed to proceed for 7 days. Aliquots of the supernatant ofinfected cells are harvested and the virus titer determined. HFF cellsin 24 well plates are infected with threefold serial dilutions ofsupernatant. The virus is allowed to adsorb to the cells for 2 hours, atwhich time the inoculum is aspirated and replaced with growth mediumcontaining 0.5% methylcellulose. The plaques are allowed to develop for7-10 days, at which time the medium is aspirated and the monolayerstained with crystal violet. The plaques are enumerated under low powermagnification. Percent inhibition is determined by comparison with thetiter from cells infected in the presence of DMSO alone.

[0553] Cellular toxicity assays: Cellular toxicity is measured in HFFcells. Cells are plated in 96 well plates at 1×10⁴ cells/well. Serialdilutions of compounds are added to the wells in DMSO, with the finalconcentration of DMSO in all wells at 1%, in a total volume of 200 μL.The plates are maintained in a 37° C. incubator for 7 days. 50 μL of asolution of XTT(sodium-3′[1-(phenyl-amino-carbonyl)-3,-tetrazolium]-bis(bis(4-methoxy-6-nitro)-benzenesulfonic acid hydrate) (3×10⁻⁴ mg/ml) is added to each well, and theplates returned to the incubator for 4 hours, after which the A₄₅₀(absorbance at wavelength of 450 nm) for each well is measured in aplate reader. (Roehm, N. W., et al J. Immunol. Meth. 142:257-265, 1991).Toxicity is determined by comparison of the OD (optical density) of awell containing compound to the OD of wells containing DMSO only.

[0554] The effect of test compounds on cellular DNA synthesis ismeasured in a ¹⁴C-thymidine incorporation assay, utilizing scintillationproximity assay technology. Cells are plated at 2×10⁴ cells/well inAmersham Cytostar 96 well scintillating microplates. The following day,serial dilutions of test compounds in DMSO are added to the wells, alongwith 0.1 μCi/well of [methyl-¹⁴C]-thymidine (specific activity 50-62mCi/mmol). The plates are counted immediately in a μBeta scintillationcounter (Wallac), to determine background, then placed in a 37° C.incubator for 7 days. The plates are removed from the incubator atintervals and the thymidine incorporation into the cellular DNAdetermined by scintillation counting. Percent inhibition is determinedby comparing ¹⁴C incorporation in wells containing test compound toincorporation in wells containing DMSO only.

[0555] Table 3 contains the results of the antiviral efficacy (HSV:EC₅₀, TC₅₀ and TI) screening results, where TI is the therapeutic index(TC₅₀/EC₅₀). TABLE 3 Antiviral Efficacy in a Yield Reduction Assay(HSV-1) Antiviral Efficacy (Vero Cells) Example EC₅₀ (μM) TC₅₀ (μM) TI(EC₅₀/TC₅₀)  60 0.5 >100 >200  57 0.81 >100 >124  56 0.7 >100 >143 2080.26 >100 >385 217 0.32 >100 >313 139 0.4 >100 >250 150 0.85 >100 >118 93 1.3 >100 >77 Reference 0.2 >100 >500 Agent (Acyclovir)

[0556] Table 4 contains the results of the antiviral efficacy (HSV:EC₅₀, TC₅₀ and TI) screening results, where TI is the therapeutic index(TC₅₀/EC₅₀). TABLE 4 Antiviral Efficacy in a Yield Reduction Assay (CMV)Antiviral Efficacy (HFF Cells) Example EC₅₀ (μM) TC₅₀ (μM) TI(EC₅₀/TC₅₀) 61 2.9 >100 >35 57 1.7 >100 >59 65 3.0 >100 >33 601.3 >100 >77 Reference 2.6 >100 >39 Agent (Ganciclovir)

[0557] Tables 3 and 4 indicates that the compounds of the presentinvention have good to excellent activity in HSV infected cells from HSVpathogenecity at μM to sub-μM concentrations.

[0558] While the forms of the invention herein disclosed constitutepresently preferred embodiments, many others are possible. It is notintended herein to mention all of the possible equivalent forms orramifications of the invention. It is understood that the terms usedherein are merely descriptive, rather than limiting, and that variouschanges may be made without departing from the spirit or scope of theinvention.

1. A compound of Formula I or a pharmaceutically acceptable salt thereof

wherein: X=O, (CH₂)_(m), S, SO, SO₂, NH, NR₈ or a chemical bond; Y=O,(CH₂)_(m), S, SO, SO₂, NH, NR₈; Z=N, NH, O, NHR₈, NR₈, S, SO, SO₂; n=aninteger of from 0 to 2; m=an integer of 1,2, or 3; R₁, R₂, R₃, R₄, R₅independently are hydrogen, halogen, hydroxyl, amino, mono ordialkylamino, cyano, nitro, alkyl groups (1-6 carbon atoms), alkoxygroups (1-6 carbon atoms), CF₃, OCF₃, aminoalkyl (1-6 carbon atoms),aminoaryl, Oaryl, or a heterocyclic ring having 5-7 atoms with 1-4hetero atoms of N, O or S; Ar=phenyl, substituted phenyl,benzoheterocyclic ring, substituted benzoheterocyclic ring, heterocyclicring, or substituted heterocyclic ring, which have substitutions R₆ orR₇; R₆ and R₇ are independently hydrogen, alkyl group (1-6 carbonatoms), cycloalkyl 3-12 carbon atoms), halogen, alkoxy, CF₃, aminoalkyl(1-6 carbon atoms), aminoaryl, or a heterocyclic ring of from 5-7 atomswith 1-4 heteroatoms of N, O or S; R₆ and R₇ may also form a ring,optionally cycloalkyl or aryl or substituted aryl; R₈ is hydrogen, alkyl(1-6 carbon atoms), cycloalkyl (3-12 carbon atoms), phenyl orsubstituted phenyl wherein the substituents are as defined above.
 2. Thecompound of claim 1 having Formula II.


3. The compound of claim 1 having Formula III.


4. The compound of claim 1 having Formula IV.


5. The compound of claim 1 having Formula V.


6. The compound of claim 1 having Formula VI.


7. The compound of claim 1 having Formula VII.


8. A pharmaceutical composition for the treatment of infection ordisease caused by a virus, which comprises an amount of the compound ofclaim 1 sufficient to provide an antivirally effective dosage of thecompound of Formula I and a pharmaceutically effective carrier.
 9. Apharmaceutical composition for the treatment of infection or diseasecaused by a virus, which comprises an amount of the compound of claim 1in the range of about 1 to about 50 mg/kg-day or up to 3 g per day and apharmaceutically effective carrier.
 10. A method of treatment ofinfection or disease caused by a virus, which comprises administering toa subject in need of such treatment a composition of claim
 1. 11. Thecomposition of claim 8 wherein the virus is a Herpes virus.
 12. Thecomposition of claim 9 wherein the virus is a Herpes virus.
 13. Themethod of claim 10 wherein the virus is a Herpes virus.
 14. 1(1-Cyclopropyl-ethyl)-(2-methoxy-dibenzofuran-3-yl)-amine 2Cyclopentyl-(9H-fluoren-2-yl)-amine 3(1-Cyclopropyl-ethyl)-(9H-fluoren-2-yl)-amine 4N³-Cyclopentyl-N²,N²-dimethyl-9H-fluorene-2,3-diamine 5Isopropyl-(2-methoxy-dibenzofuran-3-yl)-amine 6(2-Methoxy-dibenzofuran-3-yl)-(tetrahydro-thiopyran-4-yl)-amine 7Cycloheptyl-(2-methoxy-dibenzofuran-3-yl)-amine 8(1-Ethyl-propyl)-(2-methoxy-dibenzofuran-3-yl)-amine 9sec-Butyl-(2-methoxy-dibenzofuran-3-yl)-amine 10N²,N²-Dimethyl-N³-piperidin-4-yl-9H-fluorene-2,3-diamine 11N³-(1-Benzyl-butyl)-N²,N²-dimethyl-9H-fluorene-2,3-diamine 12(9H-Fluoren-2-yl)-piperidin-4-yl-amine 13(1-Benzyl-butyl)-(9H-fluoren-2-yl)-amine 14sec-Butyl-(9H-fluoren-2-yl)-amine 15(1,1-Dioxo-hexahydro-thiopyran-4-yl)-(2-methoxy-dibenzofuran-3-yl)-amine16 Dibenzofuran-2-yl-(3,3,5,5-tetramethyl-cyclohexyl)-amine 17(Decahydro-naphthalen-1-yl)-dibenzofuran-2-yl-amine 18Adamantan-2-yl-dibenzofuran-2-yl-amine 19Bicyclohexyl-4-yl-dibenzofuran-2-yl-amine 20Bicyclo[2.2.1]hept-2-yl-dibenzofuran-2-yl-amine 21(4-tert-Butyl-cyclohexyl)-dibenzofuran-2-yl-amine 22Bicyclo[3.2.1]oct-2-yl-dibenzofuran-2-yl-amine 23Cyclopentyl-dibenzofuran-2-yl-amine 24Cyclohexyl-(2-methoxy-dibenzofuran-3-yl)-amine 25Cyclohexyl-(9H-fluoren-2-yl)-amine 26Dibenzofuran-2-yl-bis-(3-methylsulfanyl-propyl)-amine 27Dibenzofuran-2-yl-bis-(3-methyl-butyl)-amine 28Dibenzofuran-2-yl-dipropyl-amine 29N³-(1,1-Dioxo-hexahydro-thiopyran-4-yl)-N²,N²-dimethyl-9H-fluorene-2,3-diamine30 N³-Isopropyl-N²,N²-dimethyl-9H-fluorene-2,3-diamine 31N²,N²-Dimethyl-N³-(tetrahydro-thiopyran-4-yl)-9H-fluorene-2,3-diamine 32N³-Cyclohexyl-N²,N²-dimethyl-9H-fluorene-2,3-diamine 33N³-Cycloheptyl-N²,N²-dimethyl-9H-fluorene-2,3-diamine 34N³-(1-Ethyl-propyl)-N²,N²-dimethyl-9H-fluorene-2,3-diamine 35N³-(1-Cyclopropyl-ethyl)-N²,N²-dimethyl-9H-fluorene-2,3-diamine 36N³-sec-Butyl-N²,N²-dimethyl-9H-fluorene-2,3-diamine 37(9H-Fluoren-2-yl)-isopropyl-amine 38(9H-Fluoren-2-yl)-(tetrahydro-thiopyran-4-yl)-amine 39Cycloheptyl-(9H-fluoren-2-yl)-amine 40Dibenzofuran-2-yl-(1,1-dioxo-hexahydro-thiopyran-4-yl)-amine 41Dibenzofuran-2-yl-piperidin-4-yl-amine 42Dibenzofuran-2-yl-isopropyl-amine 43 Cyclohexyl-dibenzofuran-2-yl-amine44 (1-Cyclopropyl-ethyl)-dibenzofuran-2-yl-amine 45Dibenzofuran-3-yl-(1,1-dioxo-hexahydro-thiopyran-4-yl)-amine 46Dibenzofuran-3-yl-piperidin-4-yl-amine 47Dibenzofuran-3-yl-isopropyl-amine 48Dibenzofuran-3-yl-(tetrahydro-thiopyran-4-yl)-amine 49Cyclohexyl-dibenzofuran-3-yl-amine 50Cycloheptyl-dibenzofuran-3-yl-amine 51(4-Chloro-benzyl)-dibenzofuran-2-yl-amine 52(4-Chloro-3-nitro-benzyl)-dibenzofuran-2-yl-amine 53Dibenzofuran-2-yl-(3-trifluoromethoxy-benzyl)-amine 54Benzo[1,3]dioxol-5-ylmethyl-dibenzofuran-2-yl-amine 55Dibenzofuran-2-yl-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-amine 56Dibenzofuran-2-yl-(3,5-dimethoxy-benzyl)-amine 57Dibenzofuran-2-yl-(4-trifluoromethyl-benzyl)-amine 58Dibenzofuran-2-yl-(2-methyl-benzyl)-amine 59Dibenzofuran-2-yl-thiophen-3-ylmethyl-amine 60Dibenzofuran-2-yl-(4-nitro-benzyl)-amine 61Dibenzofuran-2-yl-(4-methylsulfanyl-benzyl)-amine 62Dibenzofuran-2-yl-(4-methyl-benzyl)-amine 63Benzyl-dibenzofuran-2-yl-amine 64(3-Benzyloxy-benzyl)-dibenzofuran-2-yl-amine 65(1-Benzyl-butyl)-dibenzofuran-2-yl-amine 66Dibenzofuran-2-yl-[2-(2-methoxy-phenyl)-1-methyl-ethyl]-amine 673-(Dibenzofuran-2-ylamino)-2-methyl-butan-1-ol 68Dibenzofuran-2-yl-(1-ethyl-butyl)-amine 69Dibenzofuran-2-yl-(1-ethyl-propyl)-amine 70Dibenzofuran-2-yl-(1,3-dimethyl-butyl)-amine 71(1-Cyclohexyl-ethyl)-dibenzofuran-2-yl-amine 72Cyclooctyl-dibenzofuran-2-yl-amine 73Cycloheptyl-dibenzofuran-2-yl-amine 74Dibenzofuran-2-yl-(tetrahydro-thiopyran-4-yl)-amine 75Dibenzofuran-2-yl-(tetrahydro-thiophen-3-yl)-amine 76Dibenzofuran-2-yl-(1,2-dimethyl-propyl)-amine 77Dibenzofuran-2-yl-(1-methyl-butyl)-amine 78sec-Butyl-dibenzofuran-2-yl-amine 79Benzofurp[3,2-b]pyridin-8-yl-(2-fluoro-benzyl)-amine 80Benzofuro[3,3-b]pyridin-8-yl-pyridin-4-ylmethyl-amine 81Benzofuro[3,2-b]pyridin-8-yl-(2-methyl-benzyl)-amine 82N-(2-Fluoro-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 83N-Methyl-N′-quinolin-4-ylmethyl-dibenzofuran-2,8-diamine 84N-Methyl-N′-naphthanlen-1-ylmethyl-dibenzofuran-2,8-diamine 85N-(4-Methanesulfonyl-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 86N-Methyl-N′-pyridin-4-ylmethyl-dibenzofuran-2,8-diamine 87N-Methyl-N′-(2-methyl-benzyl)-dibenzofuran-2,8-diamine 88Naphthanlen-1-ylmethyl-(10H-phenothiazin-2-yl)-amine 89(4-Methanesulfonyl-benzyl)-(10H-phenothiazin-2-yl)-amine 90(3-Fluoro-2-methyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen-6-yl)-amine 91(2-Fluoro-2-methyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen-6-yl)-amine 92(10-Oxa-9-thia-1-aza-anthracen-6-yl)-qinolin-4-ylmethyl-amine 93Naphthalene-1-ylmethyl-(10-oxa-9-thia-1-aza-anthracen-6-yl)-amine 94(4-Methanesulfonyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen-6-yl)-amine 95(10-Oxa-9-thia-1-aza-anthracen-6-yl)-pyridin-4-ylmethyl-amine 96(2-Methyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen-6-yl)-amine 97Anthracen-2-yl-quinolin-4-ylmethyl-amine 98Anthracen-2-yl-(4-methanesulfonyl-benzyl)-amine 99Anthracen-2-yl-pyridin-4-ylmethyl-amine 100Anthracen-2-yl-(2-methyl-benzyl)-amine 101Dibenzo[b,e][1,4]-dioxin-2-yl-(2-fluoro-benzyl)-amine 102Dibenzo[b,e][1,4]dioxin-2-yl-(2-fluoro-benzyl)-amine 103Dibenzo[b,e][1,4]fioxin-2-yl-quinolin-ylmethyl-amine 104Dibenzo[b,e][1,4]fioxin-2-yl-naphthalen-1-ylmethyl-amine 105Dibenzo[b,e][1,4]fioxin-2-yl-(4-methanesulfonyl-benzyl)-amine 106Dibenzo[b,e][1,4]fioxin-2-yl-pyridin-4-ylmethyl-amine 1078-(3-Fluoro-2-methyl-benzylamino)-dibenzofuran-2-ol 1088-(2-Fluoro-benzylamino)-dibenzofuran2-ol 1098-(4-Methanesulfonyl-benzylamino)-dibenzofuran-2-ol 1108-[(Pyridin-4-ylmethyl)-amino]-dibenzofuran-2-ol 1118-(2-Methyl-benzylamino)-dibenzofuran-2-ol 112(8-Chloro-dibenzofuran-2-yl)-(2-fluoro-benzyl)-amine 1138-Chloro-dibenzofuran-2-yl)-naphthalen-1-ylmethyl-amine 1148-Chloro-dibenzofuran-2-yl)-(4-methanesulfonyl-benzyl)-amine 115(4-Methanesulfonyl-benzyl)-(6,7,8,9-tetrahydro-5H-carbazol-3-yl)-amine116 Pyridin-4-ylmethyl-(6,7,8,9-tetrahydro-5H-carbazol-3-yl)-amine 117Benzofuro[3,2-b]pyridin-8-yl-(3-fluoro-2-methyl-benzyl)-amine 118Dibenzofuran-2-yl-quinolin-4-ylmethyl-amine 119Dibenzofuran-2-yl-quinolin-2-ylmethyl-amine 120(4-Dimethylamino-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 121Dibenzofuran-2-yl-(4-dimethylamino-benzyl)-amine 122Dibenzofuran-2-yl-(5-nitro-thiophen-2-ylmethyl)-amine 123Dibenzofuran-2-yl-thiazol-2-ylmethyl-amine 124Benzyl-(8-fluoro-dibenzofuran-2-yl)-amine 125N-(-3-Methoxybenzyl)-N′-methyl-dibenzofuran-2,8-diamine 126N-(3,5-Dimethoxy-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 127N-(4-tert-Butyl-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 128N-Benzyl-N′-methyl-dibenzofuran-2,8-diamine 1292-[(8-Methylamino-dibenzofuran-2-ylamino)-methyl]-benzonitrile 130(4-Methoxy-benzyl)-phenoxathiin-3-yl-amine 131(8-Chloro-dibenzofuran-2-yl)-(3-methoxy-benzyl)-amine 132(3-Methoxy-benzyl)-phenoxathiin-3-yl-amine 133(3,5-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine 134(3-Fluoro-4-methoxy-benzyl)-phenoxathiin-3-yl-amine 135(4-tert-Butyl-benzyl)-phenoxathiin-3-yl-amine 136Benzyl-phenoxathiin-3-yl-amine 137(2-Ethoxy-benzyl)-phenoxathiin-3-yl-amine 138(8-Chloro-dibenzofuran-2-yl)-(3,5-dimethoxy-benzyl)-amine 139(8-Chloro-dibenzofuran-2-yl)-(3-fluoro-4-methoxy-benzyl)-amine 140Benzyl-(8-chloro-dibenzofuran-2-yl)-amine 141(9H-Fluoren-2-yl)-(4-methoxy-benzyl)-amine 142(8-Chloro-dibenzofuran-2-yl)-thiazol-2-ylmethyl-amine 143(9H-Fluoren-2-yl)-(3-methoxy-benzyl)-amine 144(3,5-Dimethoxy-benzyl)-(9H-fluoren-2-yl)-amine 145(9H-Fluoren-2-yl)-(3-fluoro-4-methoxy-benzyl)-amine 146(4-tert-Butyl-benzyl)-(9H-fluoren-2-yl)-amine 147Benzyl-(9H-fluoren-2-yl)-amine 148(9H-Fluoren-2-yl)-thiazol-2-ylmethyl-amine 149(2-Ethoxy-benzyl)-(9H-fluoren2-yl-amine 150Dibenzofuran-4-yl-(4-methoxy-benzyl)-amine 1512-[(8-Chloro-dibenzofuran-2-ylamino)-methyl]-benzonitrile 152Dibenzofuran-4-yl-(3-methoxy-benzyl)-amine 153Dibenzofuran-4-yl-(3,5-dimethoxy-benzyl)-amine 154Dibenzofuran-4-yl-(3-fluoro-4-methoxy-benzyl)-amine 155(4-tert-Butyl-benzyl)-dibenzofuran-4-yl-amine 156Dibenzofuran-4-yl-(2-ethoxy-benzyl)-amine 157N-(4-Methoxy-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 158(8-Chloro-dibenzofuran-2-yl)(4-methoxy-benzyl)-amine 159(8-Chloro-dibenzofuran-2-yl)-(2-ethoxy-benzyl)-amine 160Dibenzofuran-4-yl-(2,4-dimethyl-benzyl)-amine 161N-Methyl-N′-thiophen-3-ylmethyl-dibenzofuran-2,8-diamine 162N-Methyl-N′-pyridin-2-ylmethyl-dibenzofuran-2,8-diamine 163(2-Bromo-benzyl)-phenoxathiin-3-yl-amine 164Phenoxathiin-3-yl-quinolin-4-ylmethyl-amine 165Phenoxathiin-3-yl-thiophen-3-ylmethyl-amine 166(3-Methyl-pyridin-2-ylmethyl)-phenoxathiin-3-yl-amine 167Phenoxathiin-3-yl-pyridin-3-ylmethyl-amine 168Phenoxathiin-3-yl-pyridin-2-ylmethyl-amine 169(8-Chloro-dibenzofuran-2-yl)-thiophen-3-ylmethyl-amine 170(2-Bromo-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 171(8-Chloro-dibenzofuran-2-yl)-(3-methyl-pyridin-2-ylmethyl)-amine 172(9-Ethyl-9H-carbazol-3-yl)-thiophen-3-ylmethyl-amine 173(5-Chloro-thiophen-2-ylmethyl)-(9-ethyl-9H-carbazol-3-yl)-amine 174(9-Ethyl-9H-carbazol-3-yl)-pyridin-3-ylmethyl-amine 175(2-Bromo-benzyl)-(9H-fluoren-2-yl)-amine 176(8-Chloro-dibenzofuran-2-yl)-pyridin-4-ylmethyl-amine 177(9H-Fluoren-2-yl)-quinolin-2-ylmethyl-amine 178(9H-Fluoren-2-yl)-thiophen-3-ylmethyl-amine 179(9H-Fluoren-2-yl)-(3-methyl-pyridin-2-ylmethyl)-amine 180(9H-Fluoren-2-yl)-pyridin-4-ylmethyl-amine 181(9H-Fluoren-2-yl)-pyridin-3-ylmethyl-amine 182(9H-Fluoren-2-yl)-pyridin-2-ylmethyl-amine 183(8-Chloro-dibenzofuran-2-yl)-pyridin-3-ylmethyl-amine 184Dibenzofuran-4-yl-quinolin-4-ylmethyl-amine 185Dibenzofuran-4-yl-quinolin-2-ylmethyl-amine 186Dibenzofuran-4-yl-thiophen-3-ylmethyl-amine 187Dibenzofuran-4-yl-(3-methyl-pyridin-2-ylmethyl)-amine 188Dibenzofuran-4-yl-pyridin-4-ylmethyl-amine 189Dibenzofuran-4-yl-pyridin-3-ylmethyl-amine 190Dibenzofuran-4-yl-pyridin-2-ylmethyl-amine 191(2-Bromo-benzyl)-(8-chloro-dibenzofuran-2-yl)-amine 192(8-Chloro-dibenzofuran-2-yl)-pyridin-2-ylmethyl-amine 193N-Methyl-N′-(2,3,6-trifluoro-benzyl)-dibenzofuran-2,8-diamine 194N-Methyl-N′-(2,3,4-trifluoro-benzyl)-dibenzofuran-2,8-diamine 195N-(2,6-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 196N-(2,5-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 197N-(2,4-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 198N-(2,3-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 199N-(2,5-Dimethyl-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 200N-(2,4-Dimethyl-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 201N-(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-N′-methyl-dibenzofuran-2,8-diamine202 (3-Fluoro-2-methyl-benzyl)-phenoxathiin-3-yl-amine 203(8-Chloro-dibenzofuran-2-yl)-(2,3,6-trifluoro-benzyl)-amine 204Phenoxathiin-3-yl-(2,3,6-trifluoro-benzyl)-amine 205Phenoxathiin-3-yl-(2,3,4-trifluoro-benzyl)-amine 206(2,6-Difluoro-benzyl)-phenoxathiin-3-yl-amine 207(2,5-Difluoro-benzyl)-phenoxathiin-3-yl-amine 208(2,4-Difluoro-benzyl)-phenoxathiin-3-yl-amine 209(2,3-Difluoro-benzyl)-phenoxathiin-3-yl-amine 210(2,4-Dimethyl-benzyl)-phenoxathiin-3-yl-amine 211(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-phenoxathiin-3-yl-amine 212Benzo[b]thiophen-5-yl-(3-fluoro-2-methyl-benzyl)-amine 213(8-Chloro-dibenzofuran-2-yl)-(2,3,4-trifluoro-benzyl)-amine 214(8-Chloro-dibenzofuran-2-yl)-(2,6-difluoro-benzyl)-amine 215(8-Chloro-dibenzofuran-2-yl)-(2,5-difluoro-benzyl)-amine 216(8-Chloro-dibenzofuran-2-yl)-(2,4-difluoro-benzyl)-amine 217(9-Ethyl-9H-carbazol-3-yl)-(3-fluoro-2-methyl-benzyl)-amine 218(8-Chloro-dibenzofuran-2-yl)-(2,3-difluoro-benzyl)-amine 219(9-Ethyl-9H-carbazol-3-yl)-(2,3,6-trifluoro-benzyl)-amine 220(9-Ethyl-9H-carbazol-3-yl)-(2,3,4-trifluoro-benzyl)-amine 221(2,6-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 222(2,5-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 223(2,4-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 224(2,3-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 225(2,5-Dimethyl-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 226(2,4-Dimethyl-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine 227(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-(9-ethyl-9H-carbazol-3-yl)-amine228 (9H-Fluoren-2-yl)-(3-fluoro-2-methyl-benzyl)-amine 229(8-Chloro-dibenzofuran-2-yl)-(2,5-dimethyl-benzyl)-amine 230(9H-Fluoren-2-yl)-(2,3,6-trifluoro-benzyl)-amine 231(9H-Fluoren-2-yl)-(2,3,4-trifluoro-benzyl)-amine 232(2,5-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine 233(2,4-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine 234(2,3-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine 235(2,5-Dimethyl-benzyl)-(9H-fluoren-2-yl)-amine 236(2,4-Dimethyl-benzyl)-(9H-fluoren-2-yl)-amine 237(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-(9H-fluoren-2-yl)-amine 238(8-Chloro-dibenzofuran-2-yl)-(2,4-dimethyl-benzyl)-amine 239Dibenzofuran-4-yl-(2,5-dimethyl-benzyl)-amine 240Dibenzofuran-4-yl-(3-fluoro-2-methyl-benzyl)-amine 241N-(3-Fluoro-2-methyl-benzyl)-N′-methyl-dibenzofuran-2,8-diamine 242(8-Chloro-dibenzofuran-2-yl)-(3-fluoro-2-methyl-benzyl)-amine 243(8-Chloro-dibenzofuran-2-yl)-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-amine244 (2,5-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine 245(2,3-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine 246(2-Chloro-benzyl)-phenoxathiin-3-yl-amine 247(2-Methoxy-benzyl)-phenoxathiin-3-yl-amine 248(2-Methyl-benzyl)-phenoxathiin-3-yl-amine 249Anthracen-2-yl-(2-chloro-benzyl)-amine 250Anthracen-2-yl-(2-fluoro-benzyl)-amine 251Dibenzo[1,4]dioxin-2-yl-(2,3-dimethoxy-benzyl)-amine 252(2-Chloro-benzyl)-dibenzo[1,4]dioxin-2-yl-amine 2532-(Dibenzo[1,4]dioxin-2-ylaminomethyl)-phenol 254Dibenzo[1,4]dioxin-2-yl-(2-methoxy-benzyl)-amine 2552-[(9-Ethyl-9H-carbazol-3-ylamino)-methyl]-phenol 256(9-Ethyl-9H-carbazol-3-yl)-(2-fluoro-benzyl)-amine 257(9-Ethyl-9H-carbazol-3-yl)-(2-methyl-benzyl)-amine 258(2-Chloro-benzyl)-(9H-fluoren-2-yl)-amine 2592-[(9H-Fluoren-2-ylamino)-methyl]-phenol 260(9H-Fluoren-2-yl)-(2-methoxy-benzyl)-amine 261(9H-Fluoren-2-yl)-(2-trifluoromethyl-benzyl)-amine 262(9H-Fluoren-2-yl)-(2-fluoro-benzyl)-amine 263Dibenzofuran-4-yl-(2,5-dimethoxy-benzyl)-amine 264Dibenzofuran-4-yl-(2,3-dimethoxy-benzyl)-amine 2652-(Dibenzofuran-4-ylaminomethyl)-phenol 266Dibenzofuran-4-yl-(2-methoxy-benzyl)-amine 267(2,5-Dimethoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)-amine 268(2,3-Dimethoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)-amine 269(2-Methoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)-amine 270Dibenzofuran-2-yl-(2,5-dimethoxy-benzyl)-amine 271Dibenzofuran-2-yl-(4-methoxy-benzyl)-amine 272(2-Bromo-benzyl)-dibenzofuran-2-yl-amine 273(8-Fluoro-dibenzofuran-2-yl)-(3H-imidazol-4-ylmethyl)-amine 2742-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]-benzonitrile 275(2-Ethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 276(8-Fluoro-dibenzofuran-2-yl)-(4-methylsulfanyl-benzyl)-amine 277(2-Bromo-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 278(8-Fluoro-dibenzofuran-2-yl)-quinolin-4-ylmethyl-amine 279(8-Fluoro-dibenzofuran-2-yl)-quinolin-2-ylmethyl-amine 280Dibenzofuran-2-yl-naphthalen-1-ylmethyl-amine 281(8-Fluoro-dibenzofuran-2-yl)-naphthalen-2-ylmethyl-amine 282(8-Fluoro-dibenzofuran-2-yl)-naphthalen-1-ylmethyl-amine 283Dibenzofuran-2-yl-(2-nitro-benzyl)-amine 284Dibenzofuran-2-yl-(3H-imidazol-4-ylmethyl)-amine 2852-(Dibenzofuran-2-ylaminomethyl)-benzonitrile 286Dibenzofuran-2-yl-(2-ethoxy-benzyl)-amine 287Dibenzofuran-2-yl-(3-trifluoromethyl-benzyl)-amine 288(4-tert-Butyl-benzyl)-dibenzofuran-2-yl-amine 289Dibenzofuran-2-yl-(3-fluoro-benzyl)-amine 290(2,5-Dimethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 291(2,3-Dimethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 292(4-Benzyloxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 293(3-Benzyloxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 294(4-Chloro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 295(3-Chloro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 296(2-Chloro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 2974-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]-phenol 2983-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]-phenol 299Dibenzofuran-2-yl-(2-fluoro-benzyl)-amine 300(8-Fluoro-dibenzofuran-2-yl)-(4-methoxy-benzyl)-amine 301(8-Fluoro-dibenzofuran-2-yl)-(3-methoxy-benzyl)-amine 302(8-Fluoro-dibenzofuran-2-yl)-(2-methoxy-benzyl)-amine 303(8-Fluoro-dibenzofuran-2-yl)-(4-trifluoromethyl-benzyl)-amine 304(8-Fluoro-dibenzofuran-2-yl)-(3-trifluoromethyl-benzyl)-amine 305(4-tert-Butyl-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 306(4-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 307(3-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 308(2-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 309(8-Fluoro-dibenzofuran-2-yl)-(4-methyl-benzyl)-amine 310(8-Fluoro-dibenzofuran-2-yl)-(3-methyl-benzyl)-amine 311Dibenzofuran-2-yl-(2,6-dimethoxy-benzyl)-amine 312Dibenzofuran-2-yl-(2,4-dimethoxy-benzyl)-amine 313Dibenzofuran-2-yl-(2,3-dimethoxy-benzyl)-amine 314(4Benzyloxy-benzyl)-dibenzofuran-2-yl-amine 315Dibenzofuran-2-yl-(3-methyl-benzyl)-amine 316(3-Chloro-benzyl)-dibenzofuran-2-yl-amine 3173-(Dibenzofuran-2-ylaminomethyl)-phenol 318(2-Chloro-benzyl)-dibenzofuran-2-yl-amine 319Dibenzofuran-2-yl-(3-methoxy-benzyl)-amine 320Dibenzofuran-2-yl-(2-methoxy-benzyl)-amine 321(9H-Fluoren-2-yl)-(2-methyl-benzyl)-amine 322Dibenzofuran-4-yl-(2-methyl-benzyl)-amine 323(8-Chloro-dibenzofuran-2-yl)-(2-methyl-benzyl)-amine 324(2-Methyl-benzyl)-(10H-phenothiazin-2-yl)-amine 325Dibenzo[b,e][1,4]dioxin-2-yl-(2-methyl-benzyl)-amine 326Dibenzofuran-2-yl-(2,6-difluoro-benzyl)-amine 327Dibenzofuran-2-yl-(2,5-difluoro-benzyl)-amine 328Dibenzofuran-2-yl-(2,4-difluoro-benzyl)-amine 329Dibenzofuran-2-yl-(2,3-difluoro-benzyl)-amine 330(8-Fluoro-dibenzofuran-2-yl)-thiophen-2-ylmethyl-amine 331Dibenzofuran-2-yl-(2,5-dimethyl-benzyl)-amine 332(8-Fluoro-dibenzofuran-2-yl)-thiophen-3-ylmethyl-amine 333(8-Fluoro-dibenzofuran-2-yl)-furan-2-ylmethyl-amine 334(8-Fluoro-dibenzofuran-2-yl)-furan-3-ylmethyl-amine 335(8-Fluoro-dibenzofuran-2-yl)-(6-methyl-pyridin-2-ylmethyl)-amine 336(8-Fluoro-dibenzofuran-2-yl)-(4-methanesulfonyl-benzyl)-amine 337(8-Fluoro-dibenzofuran-2-yl)-pyridin-4-ylmethyl-amine 338(8-Fluoro-dibenzofuran-2-yl)-pyridin-3-ylmethyl-amine 339(8-Fluoro-dibenzofuran-2-yl)-pyridin-2-ylmethyl-amine 340(8-Fluoro-dibenzofuran-2-yl)-(3-fluoro-4-methoxy-benzyl)-amine 341Dibenzofuran-2-yl-(2,4-dimethyl-benzyl)-amine 342(8-Fluoro-dibenzofuran-2-yl)-(3-fluoro-2-methyl-benzyl)-amine 343(8-Fluoro-dibenzofuran-2-yl)-(2,3,6-trifluoro-benzyl)-amine 344(8-Fluoro-dibenzofuran-2-yl)-(2,3,4-trifluoro-benzyl)-amine 345(3,5-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 346(3,4-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 347(3,5-difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 348(2,6-Difluoro-benzyl(2,5-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 349(2,4-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 350(2,3-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 351(2,5-Dimethyl-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 352(2,4-Dimethyl-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 353(2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-(8-fluoro-dibenzofuran-2-yl)-amine354 (3,5-Dimethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine 355Dibenzofuran-2-yl-furan-2-ylmethyl-amine 356Dibenzofuran-2-yl-furan-3-ylmethyl-amine 357Dibenzofuran-2-yl-(6-methyl-pyridin-2-ylmethyl)-amine 358Dibenzofuran-2-yl-(4-methanesulfonyl-benzyl)-amine 359Dibenzofuran-2-yl-pyridin-4-ylmethyl-amine 360Dibenzofuran-2-yl-pyridin-3-ylmethyl-amine 361Dibenzofuran-2-yl-pyridin-2-ylmethyl-amine 362Dibenzofuran-2-yl-(3-fluoro-4-methoxy-benzyl)-amine 363Dibenzofuran-2-yl-(3-fluoro-2-methyl-benzyl)-amine 364Dibenzofuran-2-yl-(2,3,6-trifluoro-benzyl)-amine 365Dibenzofuran-2-yl-(2,3,4-trifluoro-benzyl)-amine 366Dibenzofuran-2-yl-(3,5-difluoro-benzyl)-amine 367Dibenzofuran-2-yl-(3,4-difluoro-benzyl)-amine 368Dibenzofuran-2-yl-(3,4-dimethoxy-benzyl)-amine 369Dibenzofuran-2-yl-methyl-(2-methyl-benzyl)-amine 370Dibenzothiohen-2-yl-(2,4-dimethyl-benzyl)-amine 371(4-tert-Butyl-benzyl)-dibenzothiohen-2-yl-amine 372(2-Chloro-benzyl)-dibenzothiohen-2-yl-amine 373Dibenzothiohen-2-yl-(2,6-difluoro-benzyl)-amine 374Dibenzothiohen-2-yl-(2,3,6-trifluoro-benzyl)-amine 375Dibenzothiohen-2-yl-(2-fluoro-benzyl)-amine 376Benzyl-dibenzothiohen-2-yl-amine 377Dibenzothiohen-2-yl-(4-methoxy-benzyl)-amine 378Dibenzothiohen-2-yl-(2,3-dimethoxy-benzyl)-amine 379Dibenzothiohen-2-yl-(2,5-difluoro-benzyl)-amine 380Dibenzothiohen-2-yl-(3-methoxy-benzyl)-amine 381Dibenzothiohen-2-yl-(2,3,4-trifuoro-benzyl)-amine 382(-2-Bromo-benzyl)-dibenzothiohen-2-yl-amine 383Dibenzothiohen-2-yl-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-amine 384Dibenzothiohen-2-yl-(3-fluoro-4-methoxy-benzyl)-amine 385Dibenzothiohen-2-yl-(2,5-dimethyl-benzyl)-amine 386Dibenzothiohen-2-yl-thiophen-3-ylmethyl-amine 387Dibenzothiohen-2-yl-naphthalene-1-ylmethyl-amine 388Dibenzothiohen-2-yl-(2-trifluoromethyl-benzyl)-amine 389Dibenzothiohen-2-yl-naphthalen-2-ylmethyl-amine 390Dibenzothiohen-2-yl-(2-ethoxy-benzyl)-amine 391(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3-fluoro-2-methyl-benzyl)-amine392 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2-methyl-benzyl)-amine393(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,4-dimethyl-benzyl)-amine394(4-tert-Butyl-benzyl)-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine395 (2-Chloro-benzyl)-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine396(2,6-Difluoro-benzyl)-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine397(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,3,6-trifluoro-benzyl)-amine398 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2-fluoro-benzyl)-amine399(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3,5-dimethoxy-benzyl)-amine400 Benzyl-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine 401(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(4-methoxy-benzyl)-amine 402(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,3-dimethoxy-benzyl)-amine403(2,5-difluoro-benzyl)-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine404 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3-methoxy-benzyl)-amine405(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,3,4-trifluoro-benzyl)-amine406 (2-Bromo-benzyl)-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine 407(2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine408(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3-fluoro-4-methoxy-benzyl)-amine409(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,5-dimethyl-benzyl)-amine410 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-thiophen-3-ylmethyl-amine411(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-naphthalen-1-ylmethyl-amine412(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2-trifluoromethyl-benzyl)-amine413(10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-naphthalen-2-ylmethyl-amine414 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2-ethoxy-benzyl)-amine415 (3-Fluoro-2-methyl-benzyl)-(10H-phenothiazin-2-yl)-amine 416(2,4-Dimethyl-benzyl)-(10H-phenothiazin-2-yl)-amine 417(4-tert-Butyl-benzyl)-(10H-phenothiazin-2-yl)-amine 418(2-Chloro-benzyl)-(10H-phenothiazin-2-yl)-amine 419(2,6-Difluoro-benzyl)-(10H-phenothiazin-2-yl)-amine 420(10H-Phenothiazin-2-yl)-(2,3,6-trifluorobenzyl)-amine 421(2-Fluoro-benzyl)-(10H-phenothiazin-2-yl)-amine 422(3,5-Dimethoxy-benzyl)-(10H-phenothiazin-2-yl)-amine 423Benzyl-(10H-phenothiazin-2-yl)-amine 424(4-Methoxy-benzyl)-(10H-phenothiazin-2-yl)-amine 425(2,5-Difluoro-benzyl)-(10H-phenothiazin-2-yl)-amine 426(10H-Phenothiazin-2-yl)-(2,3,4-trifluoro-benzyl)-amine 427(2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-(10H-phenothiazin-2-yl)-amine428 (3-Fluoro-4-methoxy-benzyl)-(10H-phenothiazin-2-yl)-amine 429(2,5-Dimethyl-benzyl)-(10H-phenothiazin-2-yl)-amine 430(10H-Phenothiazin-2-yl)-thiophen-3-ylmethyl-amine 431(10H-Phenothiazin-2-yl)-(2-trifluoromethyl-benzyl)-amine 432(9H-Carbazol-3-yl)-(3-fluoro-2-methyl-benzyl)-amine 433(9H-Carbazol-3-yl)-(2-methyl-benzyl)-amine 434(9H-Carbazol-3-yl)-(2,4-dimethyl-benzyl)-amine 435(4-tert-Butyl-benzyl)-(9H-carbazol-3-yl)-amine 436(9H-Carbazol-3-yl)-(2-chloro-benzyl)-amine 437(9H-Carbazol-3-yl)-(2,6-difluoro-benzyl)-amine 438(9H-Carbazol-3-yl)-(2,3,6-trifluoro-benzyl)-amine 439(9H-Carbazol-3-yl)-(3,5-dimethoxy-benzyl)-amine 440(9H-Carbazol-3-yl)-(2,3-dimethoxy-benzyl)-amine 441(9H-Carbazol-3-yl)-(2,5-difluoro-benzyl)-amine 442(9H-Carbazol-3-yl)-(2,3,4-trifluoro-benzyl)-amine 443(9H-Carbazol-3-yl)-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-amine 444(9H-Carbazol-3-yl)-(2,5-dimethyl-benzyl)-amine 445(9H-Carbazol-3-yl)-naphthalen-1-ylmethyl-amine 446(9H-Carbazol-3-yl)-naphthalen-2-ylmethyl-amine 447Dibenzofuran-2-yl-bis-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-amine448 Dibenzofuran-2-yl-bis-thiophen-3-ylmethyl-amine 449Dibenzofuran-2-yl-(4-phenoxy-benzyl)-amine 4502-Dibenzofuran-2-yl-2,3-dihydro-1H-isoindole 4512-Dibenzofuran-2-yl-1H-isoindole-1,3-dione 452Dibenzofuran-2-yl-(4-trifluoromethoxy-benzyl)-amine 453Dibenzofuran-2-yl-(2-methoxy-benzyl)-amine 454Dibenzofuran-2-yl-(3-phenoxy-benzyl)-amine 455Dibenzofuran-2-yl-methyl(2-methyl-benzyl)-amine 456Dibenzofuran-2-yl-(1-phenyl-butyl)-amine 457Dibenzofuran-2-yl-phenethyl-amine 458Dibenzofuran-2-yl-(1-phenyl-ethyl)-amine